Tetrahydrofuran → Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate

Participants

Reaction Steps

(R)-methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate (66.6AA) or (S)-methyl 3-(2,2-dimethylcyclopentyl)-4-hydroxybenzoate (66.6AB). A mixture of Rh(COD)2BF4 (Stern Chemical, 35138-22-8, 137.2 mg, 0.338 mmol) and (R)-1-[(S)-2-(R)-(ditertbutylphosphino)ferrocenyl]ethyl-bis-(3,5-bistrifluoromethylphenyl)phosphine (Solvias, SL-J210-1, 302 mg, 0.3718 mmol) was stirred in THF (300 mL) under N2 for 60 minutes and a dark red solution formed. To the resulting solution was added methyl 3-(5,5-dimethylcyclopent-1-enyl)-4-hydroxybenzoate 66.6H (41.64 g, 168.98 mmol) and TEA (10 mol %, 2.35 mL, 16.9 mmol). The resulting solution was filled with H2 (200 psi) three times and stirred at room temperature/200 psi for 2 hours. The reaction mixture was then passed through a short plug of silica gel, eluting with 1:1 hexane/EtOAc, followed by concentration afforded the desired product as a white solid (98.9A % conversion, 99% yield (41.6 g), 99% ee).

Provenance & Evidence