1-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-3,3-difluoropiperidine → HCID 89590806, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Step 1 (612 mg) in THF (20 mL) was added HF-TEA (13.58 mL) at room temperature. The solution was heated to 50° C. for 45 minutes. The reaction mixture was concentrated to remove THF and then diluted with ethyl acetate (100 mL) and water was added (100 mL). To that mixture was added Na2CO3 (14.4 g) portion wise at 0° C. When the quench was complete, the layers were separated. The organic layer was washed with 10% Na2CO3, water and brine. The aqueous layer was re-extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered and concentrated. The crude product (350 mg) was used directly in the next step. HRMS (ES+) m/z 180.1202 (M+H)+.

Provenance & Evidence