Tetrahydrofuran → HCID 11664199, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 20 mg (0.0359 mmol) of 3-[(3aS,6R,7R,7aR)-6-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-7-(4-fluorophenyl)hexahydropyrano[3,4-c]pyrrol-2(3H)-yl]cyclopent-2-en-1-one (example 3) and 19 mg (0.0430 mmol) MoOPH in 1.0 mL dry THF under nitrogen atmosphere at −78° C. was added 0.045 mL (0.15 mmol) of 2.0 M solution of LDA. The resulting mixture was stirred at −78° C. for 1 hr then quenched by the addition of sat. aq. Na2S2O3. The mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and filtered through a fritted funnel. The residue was purified by prep TLC eluting with 95/5 DCM/(10% NH4OH/methanol) to afford the title compound as a mixture of diastereomers. 1H-NMR (CD3OD): δ: 1.38 (d, 3H, J=6.5 Hz), 2.15-2.50 (m, 3H), 2.60-2.82 (m, 1H), 2.90-3.22 (m, 4H), 3.40-3.86 (m, 2H), 4.14-4.24 (m, 1H), 4.25-4.32 (m, 1H), 4.38-4.44 (m, 1H), 4.73-4.85 (m, 1H), 4.09 (q, 1H, J=6.5 Hz), 6.60-7.12 (m, 2H), 7.16-7.22 (m, 2H), 7.38 (s, 2H), 7.76 (s, 1H) ppm. MS: (MH)+574.

Provenance & Evidence