Lithium borohydride → (1S,2R,3R,4S)-3,4-Bis(hydroxymethyl)-2-(2-methylphenyl)cyclohexanol

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Reaction Conditions

Reaction Steps

To a solution of diethyl (1S,2S,3R,4S)-4-hydroxy-3-(2-methylphenyl)cyclohexane-1,2-dicarboxylate (Step G, 64.1 g, 192 mmol) in 250 mL THF under nitrogen atmosphere was slowly added LiBH4 powder (16.7 g, 767 mmol, excess) at 0° C. The resulting mixture was heated at 75° C. for 12 hr then cooled to RT. The reaction mixture was carefully quenched by addition of 30 mL water at 0° C., then 30 mL 2 N hydrochloric acid. The organic layer was separated and the aqueous was extracted with EtOAc. The combined organic extracts were washed with aqueous NaHCO3, dried over Na2SO4, filtered and the solvent evaporated under vacuum to give 43.7 g of the crude title compound which was used without further purification. 1H-NMR (CDCl3): δ: 7.30-7.13 (4H, m), 3.93-3.68 (3H, m), 3.53 (1H, dd, J1=11.2 Hz, J2=2.3 Hz), 3.27 (1H, dd, J1=11.2 Hz, J2=5.1 Hz), 2.85 (1H, t, J=10.5 Hz), 2.39 (3H, s), 2.19 (1H, m), 1.86 (3H, bs), 1.67 (2H, m), 1.55 (1H, m), 1.45 (1H, m).

Provenance & Evidence