Lithium tri-s-butylborohydride → HCID 178490600, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of 4-(4-methoxyphenyl)cyclohexanone (456.7 mg, 2.24 mmol) (prepared as described above in INTERMEDIATE 34) in THF (22 mL) was added L-Selectride (6.71 ml of a 1M solution in THF, 6.71 mmol). The reaction was allowed to warm to 0° C. over 3 hours. The reaction was then quenched with 3 mL of acetone added dropwise and 7.5 mL of H2O at 0° C. Next 3 mL of 30% H2O2 was added in a slow, dropwise manner. This mixture was stirred at 0° C. for 5 min and then diluted with EtOAc (50 mL). The organic layer was washed with water (2×25 mL) and brine (25 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 70% EtOAc/hexanes) to afford cis-4-(4-methoxyphenyl)cyclohexanol. 1H NMR (500 MHz, CDCl3): δ 7.16 (d, J=8.7 Hz, 2H), 6.85 (d, J=8.5 Hz, 2H), 4.12 (bs, 1H), 3.79 (s, 3H), 2.50 (m, 1H), 1.62-1.90 (m, 8H).

Provenance & Evidence