Sodium Fluoride → HCID 58046435, compound

Temperature

0 °C

A solution of (1R)-1-phenylethanamine (72 mL, 0.57 mol) in dichloromethane (200 mL) was cooled to 0° C. and treated with trimethylaluminum (260 mL, 0.52 mol) and the resulting solution was stirred for 1 hour at 0° C. To this solution was added a solution of 2,2-difluoro-7-oxabicyclo[4.1.0]heptane (66 g, 0.49 mol) in dichloromethane (200 mL) and the resulting mixture stirred at 0° C. for 3 hours. The reaction was then warmed to ambient temperature for 16 hours. The reaction was cooled to 0° C., treated with 103 g of sodium fluoride and then quenched with water (90 mL, slow addition). The reaction was warmed to ambient temperature, the solids filtered and the solution evaporated in vacuo. Purification by flash chromatography afforded the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.32 (s, 5H); 3.90 (q, 1H); 3.39 (ddd, 1H); 2.70 (m, 1H); 2.11 (m, 1H); 1.80 (m, 1H); 1.62 (m, 2H); 1.43 (m, 1H); 1.36 (d, 3H); 0.96 (m, 1H).

1. stirringthe resulting mixture stirred at 0° C. for 3 hours
2. temperatureThe reaction was then warmed to ambient temperature for 16 hours
3. temperatureThe reaction was cooled to 0° C.
4. customquenched with water (90 mL, slow addition)
5. temperatureThe reaction was warmed to ambient temperature
6. filtrationthe solids filtered
7. customthe solution evaporated in vacuo
8. customPurification by flash chromatography

ORD record

ord-b43f6acbf4e548e9a14a6e1f7e7cbd69

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592425B2