Water → Tert-butyl 3-((4-chlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate

HRID 1182107Notes

Reaction equation

HRID 1182107 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([CH:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[OH:20])[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59446774tert-Butyl 3-(4-chlorobenzoyl)azetidine-1-carboxylate

Product 1

HCID 69358918Tert-butyl 3-((4-chlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(4-Chloro-benzoyl)-azetidine-1-carboxylic acid tert-butyl ester (62.5 g, 210 mmol) in ethanol (1000 ml) cooled to 10° C. is treated with sodium borohydride (9.5 g, 250 mmol). The reaction mixture is allowed to warm to room temperature and stirred for 2 hours. The reaction mixture is added to water and the precipitate collected by filtration, and dried under vacuum to afford 3-[(4-Chloro-phenyl)-hydroxy-methyl]-azetidine-1-carboxylic acid tert-butyl ester. Mpt 123-125° C.

Workup

  1. filtrationthe precipitate collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-0f18db8d7d8444c2831f41243de9be78
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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