3-oxa-9-azabicyclo[3.3.1]nonan-7-ol

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

Procedure: To a stirred solution of 7-oxo-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (100 mg, 0.41 mmol) in MeOH (5 mL) was added NaBH4 (47 mg, 1.24 mmol) in one portion at room temperature. The mixture was stirred at room temperature overnight, and then quenched with sat. NaHCO3. The mixture was extracted with EtOAc (20 mL) three times. The organic layer was washed with sat. NaHCO3 and brine (20 mL) respectively. The organic layer was dried over Na2SO4, and then filtered. The solvent was concentrated under reduced pressure to give a crude product La, which was dissolved in CH2Cl2 (5 mL). Trifluoroacetic acid (2 mL) was added to the solution dropwise at 0° C. After being stirred at room temperature for 2 hours, the mixture was concentrated under reduced pressure. The residue was further dried on high-vacuum to give 3-oxa-9-aza-bicyclo[3.3.1]nonan-7-ol (Compound L) which was directly used for next step. MS: calc'd (MH+) 144, measured (MH+) 144. quenched with sat. NaHCO3 The mixture was extracted with EtOAc (20 mL) three times The organic layer was washed with sat. NaHCO3 and brine (20 mL) respectively The organic layer was dried over Na2SO4 filtered The solvent was concentrated under reduced pressure to give a crude product La, which After being stirred at room temperature for 2 hours the mixture was concentrated under reduced pressure The residue was further dried on high-vacuum