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

Temperature

50 °C

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)+.

1. concentrationThe reaction mixture was concentrated
2. customto remove THF
3. additiondiluted with ethyl acetate (100 mL) and water
4. additionwas added (100 mL)
5. additionTo that mixture was added Na2CO3 (14.4 g) portion wise at 0° C
6. customthe layers were separated
7. washThe organic layer was washed with 10% Na2CO3, water and brine
8. extractionThe aqueous layer was re-extracted with ethyl acetate (2×)
9. dry with materialThe combined organics were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-9ea9c2cd2f2e48a7a8648bf0df30ad89

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328138B2