N-(4-Aminobutyl)-N-methyl carbamic acid tert-butyl ester → [4-({3-[1-(4-Chloro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-amino)-butyl]-methyl-carbamic acid tert-butyl ester

HRID 1592500Notes

Reaction equation

HRID 1592500 reaction equation
[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:25]2[C:26]([CH:31]=O)=[N:27][CH:28]=[CH:29][CH:30]=2)([CH3:24])[CH3:23])=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:31][C:26]1[C:25]([C:22]([C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=2)([CH3:24])[CH3:23])=[CH:30][CH:29]=[CH:28][N:27]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 2756377N-(4-Aminobutyl)-N-methyl carbamic acid tert-butyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 865947683-[1-(4-Chloro-phenyl)-1-methyl-ethyl]-pyridine-2-carbaldehyde

Product 1

HCID 67273435[4-({3-[1-(4-Chloro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-amino)-butyl]-methyl-carbamic acid tert-butyl ester

Procedure

Using General Procedure B, (4-amino-butyl)-methyl-carbamic acid tert-butyl ester, 3-[1-(4-chloro-phenyl)-1-methyl-ethyl]-pyridine-2-carbaldehyde and NaBH(OAc)3 were reacted to give [4-({3-[1-(4-chloro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-amino)-butyl]-methyl-carbamic acid tert-butyl ester as a colorless oil. 1H NMR (CDCl3) δ 1.24-1.32 (m, 2H), 1.33-1.42 (m, 11H), 1.65 (s, 6H), 2.20-2.24 (m, 2H), 2.79 (s, 3H), 3.08-3.12 (m, 2H), 3.26 (s, 2H), 7.05-7.08 (m, 2H), 7.21-7.26 (m, 3H), 7.84-7.87 (m, 1H), 8.46-8.48 (m, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-e7ed6803e55c4897a73cd24bbcd143a5
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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