tert-Butanol → 1-benzylazetidine-2-carboxylic acid

HRID 1275532Notes

Reaction equation

HRID 1275532 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].C(O)(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

4

Reactant 2

HCID 6386tert-ButanolHCID 4385248Methyl 1-benzylazetidine-2-carboxylate

Product 1

HCID 2889361-benzylazetidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

N-Benzylazetidine-2-carboxylic acid methyl ester (1 g), 90 mg of t-butanol, 90 mg of water were mixed at 20 to 25° C. and 180 mg of Chirazyme L-2 were mixed and the resulting solution was heated to40° C. and stirred for 2 hours. Thereafter 1 ml of water was added thereto and washed with 4 ml of t-butyl methyl ether thrice to obtain an aqueous solution of optically active N-benzylazetidine-2-carboxylic acid. Combined organic phase gave a solution of N-Benzylazetidine-2-carboxylic acid methyl ester.

Workup

  1. additionwere mixed
  2. temperaturethe resulting solution was heated to40° C
  3. washwashed with 4 ml of t-butyl methyl ether thrice

Sources & evidence

ORD record
ord-deac43aac82040fc96f13cc7054f3190
Source dataset
uspto-grants-2000_12
Patent number
US06162621

Reaction notes

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