tert-butyl N-(4-aminobutyl)carbamate → {4-[1-(5-Methyl-pyridin-2-yl)-ethylamino]-butyl}-carbamic acid tert-butyl ester

HRID 1592511Notes

Reaction equation

HRID 1592511 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=O)[CH3:9])=[N:6][CH:7]=1.[C:11]([O:15][C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][NH2:22])([CH3:14])([CH3:13])[CH3:12].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:11]([O:15][C:16](=[O:23])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)[CH3:9])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 130686631-(5-Methyl-2-pyridinyl)ethanone

Product 1

HCID 67272693{4-[1-(5-Methyl-pyridin-2-yl)-ethylamino]-butyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 1-(5-methyl-pyridin-2-yl)-ethanone (Sundberg, R J et al. J. Am. Chem. Soc. 1969, 91, 658-668) and (4-amino-butyl)-carbamic acid tert-butyl ester in CH2Cl2 with NaBH(OAc)3 gave {4-[1-(5-methyl-pyridin-2-yl)-ethylamino]-butyl}-carbamic acid tert-butyl ester as a pale yellow oil.

Sources & evidence

ORD record
ord-fd7068b57b444109a51c4509e7b6a341
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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