Dimethyl Sulfoxide → 3-Oxo-azetidine-1-carboxylic acid tert-butyl ester

HRID 2069092Notes

Reaction equation

HRID 2069092 reaction equation
CS(C)=O.[C:5]([N:12]1[CH2:15][CH:14]([OH:16])[CH2:13]1)([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]>C(N(CC)CC)C>[O:16]=[C:14]1[CH2:15][N:12]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[CH2:13]1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterYield 61.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

A DMSO (10 mL) solution of a sulfur trioxide-pyridine complex (2.2 g; Ald) was added to a triethylamine (4 mL) solution of 1-Boc-3-(hydroxy)azetidine (500 mg; CNH) at room temperature and the resulting mixture was stirred 50° C. for 2 and half hours. The resulting mixture was stirred for approx. 10 minutes at room temperature, then the reaction mixture was poured into ice water (40 mL) and extracted with ethyl acetate (40 mL), the organic layer was dried, and the solvent was evaporated under reduced pressure to give the title compound (305 mg).

Workup

  1. stirringThe resulting mixture was stirred for approx. 10 minutes at room temperature
  2. extractionextracted with ethyl acetate (40 mL)
  3. customthe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e1847cb7d9f046cb9c34daee2c91279f
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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