Methyl 1-benzylazetidine-3-carboxylate → 1-Benzylazetidine-3-carboxylic acid

HRID 2414126Notes

Reaction equation

HRID 2414126 reaction equation
C[O:2][C:3]([CH:5]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1)=[O:4]>O>[CH2:9]([N:7]1[CH2:6][CH:5]([C:3]([OH:4])=[O:2])[CH2:8]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 18629668Methyl 1-benzylazetidine-3-carboxylate

Product 1

HCID 31613181-Benzylazetidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The N-benzylazetidine-3-carboxylic acid methyl ester product is then hydrolyzed by treatment with hot, preferably boiling, water. The completion of hydrolysis is usually marked by the transformation of the initial oily, two-phase system into a homogeneous system, and normally requires about one hour. The water may be removed from the final mixture by evaporation, and the desired product, N-benzylazetidine-3-carboxylic acid, is readily isolated as a solid. Alternatively, if it is desired to proceed with the ultimate preparation of the deprotected azetidine-3-carboxylic acid, the major part of the water may be removed (e.g., by evaporation), and the crude, wet N-benzyl acid subjected to a conventional deprotection treatment, e.g., palladium catalyzed hydrogenolysis.

Workup

  1. customThe completion of hydrolysis
  2. custominto a homogeneous system, and normally requires about one hour
  3. customThe water may be removed from the final mixture by evaporation

Sources & evidence

ORD record
ord-557fe7f1c23e4f6eac8f694ebbae61b3
Source dataset
uspto-grants-1988_01
Patent number
US04721793

Reaction notes

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