tert-butyl N-(4-aminobutyl)carbamate → {2-[(4-Tert-butoxycarbonylamino-butylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

HRID 251106Notes

Reaction equation

HRID 251106 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].[C:14]([O:18][C:19](=[O:29])[NH:20][C:21]1[C:22]([CH:27]=O)=[N:23][CH:24]=[CH:25][CH:26]=1)([CH3:17])([CH3:16])[CH3:15].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:13])[NH:7][C:8]1[C:27]([CH2:22][NH:23][CH2:24][CH2:25][CH2:26][CH2:21][NH:20][C:19]([O:18][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:29])=[N:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 4311764Sodium borohydrideHCID 10911130tert-butyl N-(2-formylpyridin-3-yl)carbamate

Product 1

HCID 67272833{2-[(4-Tert-butoxycarbonylamino-butylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure B: Reaction of (4-Aminobutyl)-carbamic acid tert-butyl ester and (2-formylpyridin-3-yl)carbamic acid tert-butyl ester in MeOH with NaBH4 gave {2-[(4-tert-butoxycarbonylamino-butylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester as a clear residue. 1H NMR (CDCl3): δ 1.44 (s, 9H), 1.53 (s, 9H), 1.55 (m, 4H), 2.67 (m, 2H), 3.13 (m, 2H), 4.07 (s, 2H), 4.53 (m, 1H), 7.15 (dd, 1H, J=6.3 Hz), 8.11 (dd, 1H, J=6.3 Hz), 8.33 (d, 1H, J=9 Hz), 10.09 (s, 1H).

Sources & evidence

ORD record
ord-3267ffe7e1474984a98060b362e43025
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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