Methanol → (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate

Participants

Reaction Steps

A solution of (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (2.62 g, 7.0 mmol) in dichloromethane (50 mL) was stirred on an ice bath and treated dropwise with diisobutylaluminum hydride (1.0 M in tetrahydrofuran, 21 mL, 21 mmol) over ca. 10 min. The solution was stirred on ice for 4 h 5 min, then was treated dropwise over 10 min with methanol (1.75 mL). The mixture was stirred on ice for 10 min, then was treated with water (2.75 mL) over ca. 1 min. The mixture was stirred at rt for 35 min, then was filtered and the gelatinous solid was triturated 3× with dichloromethane and filtered. The combined filtrates were combined and concentrated under vacuum to provide (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate as a sticky semicrystalline solid (2.41 g). MS found: (M+H—H2O)+=359.3.

Provenance & Evidence