Tetrahydrofuran → HCID 24993315, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 20 mg (0.07 mmol) of 3-[(3aR,4R,5S,7aS)-5-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}4-(4-fluorophenyl)octahydro-2H-isoindol-2-yl] cyclopent-2-en-1-one (Example 7) and 170 mg (0.39 mmol) MoOPH in ˜2 mL dry THF under nitrogen atmosphere at −78° C. was added ×x0.076 mL (0.15 mmol) of 2.0 M solution of KHMDS. The resulting mixture was stirred at −78° C. for 2hr then quenched by the addition of sat. aq. NH4Cl. The mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over drying agent and filtered. The residue was purified by prep TLC eluting with CHCl3/2N NH3 in MeOH (9/1) to afford the title compound as a mixture of diastereomers. 1H-NMR (CDCl3): δ: 7.71 (1H, s), 7.23 (2H, s), 7.00 (2H, m), 6.93 (2H, t, J=8.2 Hz), 4.85, 4.71 (H, s), 4.47 (1H, m), 4.20 (1H, m), 3.80-3.65 (1H, m),3.37 (1H, m), 3.25-3.08 (1H, m), 3.10-2.80 (3H, m), 2.58 (1H, m), 2.50-2.30 (1H, m), 2.15 (1H, m), 1.95 (2H, m), 1.35 (3H, d, J=6.0 Hz). MS: (MH)+572.5. The diastereomers were separated by HPLC on CHIRACEL AS column eluting with hexanes/EtOH (85/15) to afford the individual diastereomers.

Provenance & Evidence