(2S)-2-Amino-1,1-diphenylpropan-1-ol → HCID 86706787, compound

Participants

Reaction Conditions

Reaction Steps

(6-Hydroxy-1-benzofuran-3-yl)acetic acid (25 g), dichloro[(+)-1,2-bis((2R,5R)-2,5-diisopropylphosphorano)benzene]ruthenium (II)-N,N-dimethylformamide complex (19.1 mg) and (S)-2-amino-1,1-diphenylpropan-1-ol (29.5 g) were weighted in an autoclave and substituted with argon. Dehydrated methanol (250 mL) was added and the mixture was purged with hydrogen, pressurized under a hydrogen pressure (1.0 MPa), and reacted at 35° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, methanol (109 mL) and N,N-dimethylformamide (27 mL) were added, and the mixture was dissolved by heating at 50° C. Isopropyl ether (200 mL) was added dropwise at 60° C., seed crystal was added, and isopropyl ether (369 mL) was added dropwise. The mixture was cooled to room temperature, stirred for 4 hr and stirred for 1 hr under ice-cooling, and the solid was collected by filtration. The solid was dried at 60° C. under reduced pressure to give the title compound (38.98 g). 99.8% de.

Provenance & Evidence