benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.5 g benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate in 80 mL 33% aqueous ammonia solution was stirred 20 h in a closed vessel. The reaction was cooled and extracted with dichlormethane. The organic layer was washed with sodium chloride solution and evaporated to give 6.1 g of the desired product. The reaction was cooled extracted with dichlormethane The organic layer was washed with sodium chloride solution evaporated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (10.5 g, 47.9 mmol) and pyridine-hydrogen fluoride (14.2 g, 144.0 mmol) were added to a Teflon bottle containing dichloromethane and stirred vigorously overnight. After 20 hours, the reaction was slowly and carefully quenched with excess saturated solution of NaHCO3 over several minutes and allowed to stir for one hour, and then the organic layer was isolated and washed with NaHCO3 and a solution of brine. The combined organic layers were dried over MgSO4, filtered and evaporated to yield an oil. This crude oil was purified on silica gel using ethyl acetate-hexane to produce 2.0 g (17% isolated yield) of the desired product as an oil. After 20 hours carefully quenched with excess saturated solution of NaHCO3 over several minutes to stir for one hour the organic layer was isolated washed with NaHCO3 The combined organic layers were dried over MgSO4 filtered evaporated to yield an oil This crude oil was purified on silica gel to produce