Water → HCID 18951279, compound

Participants

Reaction Conditions

Reaction Steps

A 1 L round-bottomed flask was charged with NaBH4 (3.2 g, 84.5 mmol) in THF (300 mL) and then cooled to −20° C. Water (50 mL) was added to the reaction mixture followed by the dropwise addition of 2 (6.3 g, 16.9 mmol) in THF (50 mL) over 1 h. After an additional 30 min, the cold reaction mixture was quenched by the careful addition of 1M HCl (60 mL). The reaction mixture was then diluted with EtOAc. The organic phase was washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was chromatographed by flash silica gel chromatography (4:1 hexanes/EtOAc) to afford 5.9 g (93%) of 3. 1H NMR (CDCl3, 300 MHz), mixture of rotomers: δ4.48 (m, 1H), 4.32 (m, 1H), 4.08 (m, 1H), 3.55 (m, 0.4H), 3.38 (m, 0.6H), 3.28 (app dd, J=11.7, 4.2 Hz, 1H), 2.32 (m, 1H), 2.18 (m, 1H), 2.04 (m, 2H), 1.67 (m, 1H), 1.45 (s, 9H), 0.85 (s, 9H), 0.05 (s, 6H) ppm.

Provenance & Evidence