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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1602187Generated: October 30, 2026

m-Chloroperbenzoic acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

https://huagongshe.com/reaction/1602187

Reaction equation

Participants

RoleNameHCIDCharge
Reactantm-Chloroperbenzoic acidHCID 70297—
Reactanttert-Butyl 3,6-dihydropyridine-1(2H)-carboxylateHCID 13094787—
SolventDichloromethaneHCID 6344—
Producttert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylateHCID 21991116—

Reaction Steps

A mixture of N-tert-butoxycarbonyl-1,2,3,6-tetrahydropyrdine (23.6 g, 129 mmol), and m-chloroperbenzoic acid (46 g, 193 mmol) in dichloromethane (600 ml) at 0° C. was stirred and allowed to reach room temperature overnight. Washing with 5% aqueous sodium sulfite (700 ml), 3% aqueous sodium hydrogen carbonate (700 ml), 1 M aqueous sodium hydroxide (700 ml), and, finally, water (700 ml). Drying and evaporation was followed by purification by column chromatography on silica gel with 3% ethanol in dichloromethane. The title compound was obtained as a colorless oil. Yield 8.4 g, 33%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05981539
Source datasetuspto-grants-1999_11
ORD IDord-1120bb301c47428080ff867513c9b1f2
Source noteuspto-grants-1999_11