Sodium borohydride → Cyclopropyl-{4-[(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

HRID 251065Notes

Reaction equation

HRID 251065 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH:8]1[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]1[C:19]([CH:25]=O)=[N:20][CH:21]=[C:22]([CH3:24])[CH:23]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:16])[N:7]([CH:8]1[CH2:9][CH2:10]1)[CH2:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:25][C:19]1[C:18]([CH3:17])=[CH:23][C:22]([CH3:24])=[CH:21][N:20]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehydeHCID 67271617(4-Amino-butyl)-cyclopropylcarbamic acid tert-butyl ester

Product 1

HCID 67272811Cyclopropyl-{4-[(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using General Procedure B, (4-amino-butyl)-cyclopropyl-carbamic acid tert-butyl ester and 3,5-dimethyl-pyridine-2-carbaldehyde in MeOH were reacted with NaBH4 to obtain cyclopropyl-{4-[(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as a colorless oil (0.217 g, 89%). 1H NMR (CDCl3) δ 0.52-0.58 (m, 2H), 0.68-0.74 (m, 2H), 1.44 (s, 9H), 1.53-1.65 (m, 4H), 2.26 (s, 6H), 2.45-2.50 (m, 1H), 2.70 (t, 2H, J=6.9 Hz), 3.19 (t, 2H, J=7.2 Hz), 3.82 (s, 2H), 7.23 (s, 1H), 8.20 (s, 1H).

Sources & evidence

ORD record
ord-81c87f187539489cb7ee03a5211ad0dc
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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