Tetrahydrofuran → HCID 53758367, compound

Participants

Reaction Steps

To a stirred solution of ester from Example 59 (1.84 g, 6.13 mmol) in dry THF (15 mL) was added 2M lithium borohydride in THF (5.0 mL, 10.0 mmol) dropwise under nitrogen. The solution was stirred overnight, then quenched by the dropwise addition of methanol (25 mL) and stirred 4 h. The reaction was concentrated, poured into 10% aqueous citric acid (100 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extract was dried over MgSO4 and concentrated. The resulting residue was purified by chromatography (silica gel, ethyl acetate-hexanes, 50:50, 75:25), followed by crystallization from ethyl acetate-hexanes to provide the desired product. (510 mg). m.p=122°-123.5° C.; NMR (300 MHz, DMSO-d6) 1.29 (3H, d, J=7.0 Hz), 2.28 (3H, s), 2.32 (3H, s), 3.08 (2H, m), 3.35 (2H, m), 4.65 (1H, t, J=5.3 Hz), 5.23 (1H, q, J=7.0 Hz), 6.70 (1H, t, J=5.9 Hz), 6.73 (1H, m), 9.03 (1H, s); MS: (M+H)+ =259

Provenance & Evidence