Methyl 1-benzylazetidine-2-carboxylate → 1-benzylazetidine-2-carboxylic acid

HRID 2187333Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:8][CH2:7][N:6]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:4]>COC(C)(C)C.O>[CH2:9]([N:6]1[CH2:7][CH2:8][CH:5]1[C:3]([OH:4])=[O:2])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 40 °C

Procedure

N-Benzylazetidine-2-carboxylic acid methyl ester (1.4 g) was dissolved in 40 ml of t-butyl methyl ether at 20 to 25° C. and stirred for one minute and 70 mg of Enzyme (Chirazyme L-2) suspended in 2 ml of water was poured thereto and the resulting solution was heated to 40° C. and stirred for 14 hours. Settled solution was separated into an aqueous phase and an organic phase. The aqueous phase was washed twice with t-butyl methyl ether (5 ml) to yield an aqueous solution of optically active N-benzylazetidine-2-carboxylic acid and a combined organic phase of N-Benzylazetidine-2-carboxylic acid methyl ester.

Workup

additionwas poured
stirringstirred for 14 hours
customSettled solution was separated into an aqueous phase
washThe aqueous phase was washed twice with t-butyl methyl ether (5 ml)

Sources & evidence

ORD record: ord-7d9682eaaa9f43acb95999dfa01ea36f
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410279B1

Reaction notes

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