Lithium borohydride → ((1S,2R,3R,4S)-4-((R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-3-(4-fluorophenyl)cyclohexane-1,2-diyl)dimethanol

To a solution of 9.2 g (15.9 mmol) diethyl(1S,2S,3R,4S)-4-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-3-(4-fluorophenyl)cyclohexane-1,2-dicarboxylate (step F) in 100 mL THF under nitrogen atmosphere at RT was added 2 g (112.4 mmol, excess) LiBH4 powder. The resulting mixture was heated at 68° C. for 2 hr then cooled to RT. The reaction mixture was carefully quenched by the addition of 30 mL water, then extracted with EtOAc. The combined organic extracts were dried over drying agent, filtered and the solvent evaporated under vacuum to give 7.5 g of the crude title compound as an oil which was used without further purification. 1H-NMR (CDCl3): δ: 7.70 (1 H, s), 7.20 (2 H, s), 7.00 (2 H, m), 6.87 (2 H, t, J=8.2 Hz), 4.20 (1 H, q, J=6.0 Hz), 3.78 (1 H, m), 3.67 (1 H, m), 3.52 (1 H, m), 3.30-3.20 (2 H, m), 2.58 (1 H, t, J=11.9 Hz), 2.32 (1 H, m), 1.87 (1 H, m), 1.87 (1 H, m), 1.65 (1 H, m), 1.58-1.35 (3 H, m), 1.30 (3 H, t, J=6.0 Hz).

1. temperaturethen cooled to RT
2. customThe reaction mixture was carefully quenched by the addition of 30 mL water
3. extractionextracted with EtOAc
4. customThe combined organic extracts were dried
5. customover drying agent
6. filtrationfiltered
7. customthe solvent evaporated under vacuum

ORD record

ord-080e712fad2c49e780259233222154c7

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345083B2