3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-(4-fluorophenyl)-3-hydroxyazetidine-1-carboxylate

HRID 72406Notes

Reaction equation

HRID 72406 reaction equation
[C:1]([N:8]1[CH2:11][C:10](=[O:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:13][C:14]1[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:10]2([OH:12])[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]2)=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418676HCID 178418676, compound

Product 1

HCID 65813955tert-Butyl 3-(4-fluorophenyl)-3-hydroxyazetidine-1-carboxylateYield 110.7%

Procedure

The title compound (D29) (819.5 mg) was prepared according to the experimental procedure described in Description 28 starting from 1-Boc-3-azetidinone (500 mg, 2.77 mmol) and 4-Fluorophenylmagnesiumbromide (2M in diethylether) (1.67 ml, 3.33 mmol)).

Sources & evidence

ORD record
ord-0ce4e0a2480c433d9896be7d1fb93e51
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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