HCID 22220462, compound → 3-((tert-Butyldimethylsilanyl)oxy)azetidine

Participants

Reaction Steps

Add 20% palladium hydroxide on activated carbon (0.946 g) and ethanol (20 mL) to a Parr pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the mixture at RT for 15 min. Vent the hydrogen from the reaction vessel and purge the reaction vessel with nitrogen. Add 1-benzhydryl-3-(tert-butyl-dimethylsilanyloxy)-azetidine (3.89 g, 0.0110 mol) and ethanol (80 mL) to the pressure vessel. Purge the reaction vessel with nitrogen, pressurize the reaction mixture with hydrogen (400 kPa), seal the vessel and agitate the reaction at RT for 6 h. Turn off the agitation, vent the excess hydrogen from the vessel and purge the vessel with nitrogen. Sample the reaction mixture for analysis. Once the reaction is shown to be complete, filter the reaction mixture to remove the catalyst, concentrate and purify (silica gel chromatography, eluting with 5:95 to 10:90 2 M ammonia in methanol:DCM) to give the title compound (889 mg, 43%).

Provenance & Evidence