(3R)-pyrrolidin-3-ol hydrochloride → HCID 24984105, compound

Participants

Reaction Steps

4′-(2-Oxo-1-oxa-3-aza-spiro[4.5]dec-3-ylmethyl)-biphenyl-4-carbaldehyde (50 mg, 0.143 mmol) was mixed with (R)-(−)-3-pyrrolidinol hydrochloride (20 mg, 0.157 mmol) in DCE (2.5 mL). Na(OAc)3BH was added as a solid at room temperature and the reaction was stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM (3×5 mL), the combined organic phases were washed with brine (5 mL), dried over sodium sulfate and concentrated. The crude residue was purified on silica gel eluting with DCM containing 0.5˜2% 2M ammonia in methanol to give the product as off-white solid (34 mg, 56.5%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.59 (dd, 4H), 7.38 (d, 2H), 7.29 (d, 2H), 4.42 (s, 2H), 4.37 (m, 1H), 3.69 (s, 2H), 3.13 (s, 2H), 2.87 (m, 1H), 2.67 (d, 1H), 2.58 (dd, 1H), 2.37 (m, 2H), 2.2 (m, 1H), 1.76 (m, 4H), 1.51 (m, 6H).

Provenance & Evidence