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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2069092Generated: October 29, 2026

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

https://huagongshe.com/reaction/2069092

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantTert-butyl 3-hydroxyazetidine-1-carboxylateHCID 2756801—
SolventTriethylamineHCID 8471—
Product3-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 151940461.7%

Reaction Conditions

Temperature50 °C

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08299055B2
Source datasetuspto-grants-2012_10
ORD IDord-e1847cb7d9f046cb9c34daee2c91279f
Source noteuspto-grants-2012_10