Ammonium Chloride → (2S,5R)-5-Ethyl-4-(phenylmethyl)-2-morpholinemethanol

Participants

Reaction Steps

To a solution of (2R)-2-[(phenylmethyl)amino]-1-butanol (10.06 g, 56.1 mmol) in 1,2-dichloroethane (DCE) (250 mL) was added (R)-(−)-epichlorohydrin (6.75 g, 72.9 mmol) followed by lithium perchlorate (5.97 g, 56.1 mmol) under nitrogen. The reaction was stirred for 2 days at room temperature, then sodium ethoxide (52.4 mL, 140 mmol) was added and the reaction continued to stir for 3 days. Saturated NH4Cl was added, and the product was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, and concentrated to afford the title compound (16.2 g) as a colorless oil. LC-MS (ES) m/z=236 [M+H]+.

Provenance & Evidence