Chemoselective Reductive Amination of Carbonyl Compounds for the Synthesis Synthesis of Tertiary Amines Using SnCl 2 2H 2 O/PMHS/MeOH
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1 Supporting information Chemoselective Reductive Amination of Carbonyl Compounds for the Synthesis Synthesis of Tertiary Amines Using SnCl 2 2H 2 O/PMHS/MeOH Onkar S. ayal, Vinod Bhatt,, Sushila Sharma,, and eeraj Kumar *,, atural Product Chemistry and Process Development Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur, Himachal Pradesh , India Academy of Scientific and Innovative Research, Anusandhan Bhawan, 2 Rafi Marg, ew Delhi , India * neerajnpp@rediffmail.com, neeraj@ihbt.res.in. Contents Optimization of reaction conditions S2 Mechanistic study.s3 1 H& 13 C MR Spectra... S10 FTIR Spectra of Unknown compounds S56 S1
2 Table S1: Optimisation of Reaction Conditions for DRA of Anisaldehyde with -Methyl aniline a O H CHO catalyst + reducing agent solvent, 70 o C, 6 h O Entry Catalyst Reducing agent Solvent Yield b (%) 1 FeCl 2 4H 2 O PMHS MeOH 4 2 SnCl 2 2H 2 O PMHS MeOH 86 3 SnCl 2 2H 2 O PMHS MeOH 40 c 4 SnCl 2 2H 2 O PMHS MeOH 60 d 6 SnCl 2 2H 2 O Hantzsch Ester MeOH R 7 SnCl 2 2H 2 O HCOOH MeOH R 8 SnCl 2 2H 2 O HCOOH 4 MeOH 32 9 SnCl 2 2H 2 O PMHS MeOH 62 e 10 SnCl 2 2H 2 O PMHS MeOH 87 f 11 SnCl 2 PMHS Toluene 10 g 12 SnCl 2 PMHS MeOH 50 g 13 SnCl 2 PMHS MeOH 61 h 14 SnCl 2 PMHS MeOH 65 i 15 SnCl 2 PMHS MeOH 52 j a Reaction conditions: Catalyst (20 mol%), 1 (1.1 mmol), 2 (1 mmol), reducing agent (2 mmol), MeOH (3 ml), 70 C, 6 h. b GC yield using hexadecane as internal standard. c Quantity of catalyst used was 5 mol%. d Quantity of catalyst used was 10 mol%. e The reaction was carried out using 1 mmol PMHS. f The reaction was carried out using 2.5 mmol PMHS. g The reaction was carried out in anhydrous condition under 2 atmosphere. h The reaction was carried out under anhydrous conditions with 1 equivalent water. i The reaction was carried out under anhydrous conditions with 3 equivalent water. j The reaction was carried out under anhydrous conditions with 5 equivalent water. Table S2: Tested Aliphatic Amines for Reductive Amination with Anisaldehyde A1 H O H A2 H A3 H A4 H A5 Amine A1 A2 A3 A4 A5 Yield nr nr nr nr nr S2
3 Mechanistic investigation (I) Evidences for formation of complex A SnCl 2 2H 2 O and MeOH as mixed in 1:1 ratio and the mixture was analysed with IR. The appearance of new band at 416 cm -1 due to v Sn O bond indicated the formation of complex A. 1 Moreover the absence of band in the region cm -1 for v Sn-O bond omitted the formation of tin alkoxides. 2 a) IR study for formation of complex A 120 %T SnCl2.2H2O Figure 1a. FT-IR spectra of SnCl 2 2H 2 O /cm S3
4 %T SnCl2.2H2O Figure 1b. FT-IR spectra of SnCl 2 2H 2 O (region cm -1 ) /cm 120 %T SnCl2+ MeOH (1:1) Figure 2a. FT-IR Spectra of [Sn x Cl y (MeOH) z ] 2H 2 O (Complex A) /cm S4
5 %T SnCl2+ MeOH (1:1) Figure 2b. FT-IR Spectra of [Sn x Cl y (MeOH) z ] 2H 2 O (Complex A) (region cm -1 ). Reference (a) Dubey, R. K.; Singh, A. P. J. Coord. Chem. 2013, 66, (b) Anderson. A.; Gebbie, H. A. J.Organometal. Chern. 1964, Basu, S.; Gupta, G.; Das, B.; Rao, K. M. J. Organomet. Chem. 2010, 695, (2) UV-Vis study for formation of complex A /cm 214 nm S5
6 Figure 3. UV-Vis spectra of SnCl 2 2H 2 O methanol complex. (3) ESI-MS study of complex of hydrated stannous chloride and methanol (complex A) Figure 4. ESI(+)-Mass spectra of hydrated stannous chloride and methanol complex. We found several stannous complexes by ESI-MS analysis mmol of hydrated stannous chloride dissolved in 1.0 ml of MeOH, the mixture was subjected to ESI-(+)-MS. Similar results were obtained throughout the reaction time (15 min to 6 h). The cluster masses of three major species were observed at m/z 293, 543 and 719 for [SnCl 3 (MeOH)] 2H 2 O, [Sn 2 Cl 5 (MeOH) 3 ] 2H 2 O and [Sn 3 Cl 6 (MeOH) 3 ] 3H 2 O, respectively (Figure 4). S6
7 (II) 1 H MR study for activation of PMHS SnCl 2 2H 2 O (0.20 mmol) and PMHS (1mmol) was added to CD 3 OD in test tube and stirred at 70 o C. The reaction mixture was drawn from test tube after 1 h and 2 h respectively analysed by 1 H MR of which showed the disappearance of Si-H signal observed at 4.75 ppm after 2 h which supported the activation of PMHS by complex (A). c) b) a) Si-H ppm Scale: ppm/cm, Hz/cm Figure 5. 1 H MR of a) PMHS in CD 3 OD; b) PMHS+SnCl 2 2H 2 O in CD 3 OD after 1 h; c) PMHS+SnCl 2 2H 2 O in CD 3 OD after 2 h. S7
8 FTIR study of PMHS activation by SnCl 2 2H 2 O. SnCl 2 2H 2 O, PMHS and MeOH were mixed in 1:1:1 ratio and the mixture was heated at 70 o C. Disappearance of Si-H band at 2162 cm -1 was observed by FTIR. 120 %T Si-H PMHS /cm Figure 6. FTIR spectra of PMHS %T KO286A-1H /cm Figure 7. FTIR spectra of PMHS and hydrated stannous chloride in methanol S8
9 (III) ESI-MS study for intermediate formation (a)esi-(+)-ms study of intermediate of carbonyl compound and amine in the absence of PMHS. To a stirred solution of SnCl 2 2H 2 O (0.20 mmol) in MeOH (3mL) were added anisaldehyde (1.1 mmol), -methylaniline (1.0 mmol) at room temperature and then the temperature was raised to 70 o C for 3h, An aliquot of reaction mixture was drawn and analyzed by ESI-MS. O Figure 8. ESI-MS-MS spectra of iminium ion (molecular weight - 226). To a stirred SnCl 2 2H 2 O (0.20 mmol) in MeOH (3mL) were added cyclopentanone (1.1 mmol), - methylaniline (1.0 mmol) at room temperature and then the temperature was raised to 70 o C for 3h, An aliquot of reaction mixture was given for ESI-MS study. Figure 9. ESI-MS-MS spectra of enamine [ (M+H) + 174]. S9
10 H and 13 C MR spectra of synthesized compounds -(2-Bromobenzyl)--methylaniline (3a) in CDCl 3 Br 3a S10
11 (3-Chlorobenzyl)--methylaniline (3b) in CDCl 3 Cl S11
12 (4-Bromo-2-flourobenzyl)--methylaniline (3c) in CDCl 3 Br F ppm S12
13 (4-Bromobenzyl)--methylaniline (3d) in CDCl 3 Br S13
14 (4-Chlorobenzyl)--methylaniline (3e) in CDCl 3 Cl S14
15 (4-Methoxybenzyl)--methylaniline (3f) in CDCl 3 O S15
16 (3-Hydroxy-4-methoxybenzyl)--methylaniline (3g) in CDCl 3 O OH ppm S16
17 (3-Hydroxybenzyl)--methylaniline (3h) in CDCl 3 OH S17
18 (3-Iodo-4,5-dimethoxybenzyl)--methylaniline (3i) in CDCl 3 O O I S18
19 (3, 4, 5-trimethoxybenzyl)--methylaniline (3j) in CDCl 3 O O O S19
20 (2,3, 4, -Trimethoxybenzyl)--methylaniline (3k) in CDCl 3 O O O S20
21 (3-Ethoxy-4-hydroxybenzyl)--methylaniline (3l) in CDCl 3 HO OEt S21
22 (2,4-Dimethoxybenzyl)--methylaniline (3m) in CDCl 3 O O S22
23 (2-Hydroxy-4-methoxybenzyl)--methylaniline (3n) in CDCl 3 O OH S23
24 (2-Hydroxy-3-methoxybenzyl)--methylaniline (3o) in CDCl 3 O OH S24
25 (2-Hydroxy-3-methoxy-5-prop-2-eneylbenzyl)--methylaniline (3p) in CDCl 3 O OH S25
26 (4-Methoxycinnamyl)--methylaniline (3q) in CDCl 3 O S26
27 Cinnamyl--methylaniline (3r) in CDCl 3 S27
28 (3-Phenyl-2-methylpropeneyl)--methylaniline (3s) in CDCl 3 S28
29 Furfuryl--methylaniline (3t) in CDCl 3 O S29
30 (1-Anthracenylmethyl)--methylaniline (3u) in CDCl 3 S30
31 (3-Phenylpropyl)--methylaniline (3v) in CDCl 3 S31
32 (4-Methoxybenzyl)--ethylaniline (3w) in CDCl 3 O S32
33 ,-Dibenzyl-4-methoxyaniline (3x) in CDCl 3 O S33
34 Cyclopentyl--methylaniline (5a) in CDCl 3 S34
35 Cyclohexyl--methylaniline (5b) in CDCl 3 S35
36 (4-Methylcyclohexyl)--methylaniline (5c) in CDCl ppm S36
37 (3-Methylcyclohexyl)--methylaniline (5d) in CDCl ppm ppm S37
38 Cyclopentyl-, -diphenylamine (5e) in CDCl 3 S38
39 (4-Methylcyclohexyl)-, -diphenylamine (5f) in CDCl ppm S39
40 (1-Methylbenzyl)--methylaniline (5g) in CDCl 3 S40
41 (1-phenylethyl)--methyl-4-fluoroaniline (5h) in CDCl 3. F S41
42 (1-(4-bromobenzyl)ethyl)--methylaniline (5i) in CDCl 3 Br S42
43 (6-Chloropyridin-3-yl)--(4-methoxybenzyl)amine (7a) in CDCl 3 Cl O H S43
44 Benzyl-(6-chloropyridin-3-yl)amine (7b) in CDCl 3 Cl H S44
45 Benzyl-4-methoxyaniline (7c) in CDCl 3. O H S45
46 (4-Methoxybenzyl)-4-methoxyaniline (7d) in CDCl 3 O H O S46
47 (4-Methoxycinnamyl)--methylaniline (7e) in CDCl 3 O H S47
48 (3,4,5-Trimethoxybenzyl)-4-bromoaniline (7f) in CDCl 3 Br MeO MeO OMe H S48
49 (4-Benzylaminophenyl)ethanone (7g) in CDCl 3 H O S49
50 Benzyl-4-carboxyaniline (7h). in CD 3 OD COOH H S50
51 Benzyl-4-nitroaniline (7i) in CDCl 3 O 2 H S51
52 (1-Phenylethyl) aniline (7j) in CDCl 3 H S52
53 Isobutylaniline (7k) in CDCl 3 H S53
54 Isobutyl-4-methoxyaniline (7l) in CDCl 3 H O S54
55 Cyclohexylaniline (7m) in CDCl 3 H S55
56 FTIR-Spectra of Unknown compounds -(3-Iodo-4,5-dimethoxybenzyl)--methylaniline (3i): 130 %T nkon259b -(2,4-Dimethoxybenzyl)--methylaniline (3m); /cm S56
57 S57 -(2-Hydroxy-3-methoxy-5-prop-2-eneylbenzyl)--methylaniline (3p): -(4-Methoxycinnamyl)--methylaniline (3q): /cm %T nkon253b /cm %T nkon265b
58 S58 -(3-Phenyl-2-methylpropeneyl)--methylaniline (3s): -(1-Anthracenylmethyl)--methylaniline (3u): /cm %T nkon256br /cm %T nkon254c
59 S59 -(3-Methylcyclohexyl)--methylaniline (5d): -Cyclopentyl--biphenylamine (5e): /cm %T nkon237b /cm %T nkon262a
60 S60 -(1-phenylethyl)--methyl-4-fluoroaniline (5h): /cm %T nkon278a /cm %T nkonrm3
61 S61
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