Sodium Hydroxide → HCID 57707243, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of 66.48C (0.4115 g, 1.129 mmol) in dry THF (10 mL) at 0° C. was added LAH (1.0M in THF) (2.30 mL, 2.3 mmol) dropwise. Upon complete addition, the reaction was maintained at 0° C. and was monitored by TLC and LCMS. After 45 minutes, 1N NaOH was added to quench the reaction. The resulting mixture was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate, filtration, and concentration, the residue was purified by flash chromatography (SiO2 gel 60, eluted with 0%-50% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to a colorless oil as 66.48D (317.1 mg, 83% yield). MS ESI (pos.) m/e: 319.0 (M−H2O)+. Chiral separation of 66.48D was accomplished on Chiracel-OD (3% IPA in hexane) to provide 66.48E (peak 1) and 66.48F (peak 2). Both enantiomers were used to synthesize example compounds, and both enantiomers gave active compounds.

Provenance & Evidence