tert-butyl N-(4-aminobutyl)carbamate → {4-[1-(3-Methylpyridin-2-yl)-ethylamino]-butyl}-carbamic acid tert-butyl ester

HRID 1592504Notes

Reaction equation

HRID 1592504 reaction equation
[CH3:1][C:2]1[C:3]([C:8](=O)[CH3:9])=[N:4][CH:5]=[CH: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:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:9])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 130686691-(3-Methylpyridin-2-yl)ethan-1-one

Product 1

HCID 67272873{4-[1-(3-Methylpyridin-2-yl)-ethylamino]-butyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B, 1-(3-methylpyridin-2-yl)-ethanone (Sundberg, R J et al. J. Am. Chem. Soc. 1969, 91, 658-668), (4-aminobutyl)-carbamic acid tert-butyl ester and NaBH(OAc)3 were reacted in CH2Cl2 to obtain {4-[1-(3-methylpyridin-2-yl)-ethylamino]-butyl}-carbamic acid tert-butyl ester.

Sources & evidence

ORD record
ord-aa63716ece674a1ab12f919c40c12881
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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