Sodium borohydride → Tert-butyl 4-((4-bromophenyl)(hydroxy)methyl)piperidine-1-carboxylate

HRID 1726115Notes

Reaction equation

HRID 1726115 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[OH:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 228905261-Boc-4-(4-Bromobenzoyl)piperidine

Product 1

HCID 57603260Tert-butyl 4-((4-bromophenyl)(hydroxy)methyl)piperidine-1-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(4-bromobenzoyl)-piperidine-1-carboxylic acid tert-butyl ester (1.47 g, 4.00 mmol) in absolute EtOH (25 mL) was added NaBH4 (227 mg, 6.00 mmol). The mixture was stirred at room temperature for 2 hours. Standard work-up and purification gave 4-[(4-bromo-phenyl)-hydroxymethyl]-piperidine-1-carboxylic acid tert-butyl ester as a white solid (1.480 g, 100%). 1H NMR (CDCl3) δ 1.07-1.27 (m, 2H), 1.62-1.72 (m, 1H), 1.88 (d, 1H, J=13.2 Hz), 2.35 (d, 1H, J=3.3 Hz), 2.50-2.65 (m, 2H), 4.04-4.13 (m, 2H), 4.33 (dd, 1H, J=7.2, 3.3 Hz), 7.16 (d, 2H, J=8.4 Hz), 7.45 (d, 2H, J=8.4 Hz).

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-8b0c1c2a2ced4764a5809e7507d69f6c
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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