Benzaldehyde → (2R)-2-(Benzylamino)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of (2R)-2-amino propanol (1.2 equivalents), benzaldehyde (1 equivalent), NaHCO3 (1.5 equivalents), and MeOH, (˜1 M) was heated at reflux for 4 hours and then cooled to 0° C. Sodium borohydride (4.8 equivalents) was added portionwise to the stirred reaction mixture during a period of 2 hours at ca. 10° C. The whole was stirred at room temperature for 4 hours. The insoluble materials were filtered off and then the filtrate was concentrated to dryness. The residue was dissolved in CH2Cl2, and the solution was washed successively with water (2×) and brine (1×). The organic extracts were collected and dried (Na2SO4). The solvent was evaporated to give the desired product as a colorless oil, which solidified on standing and was used in the next step without further purification. GC/MS: 134 (100%, M+−CH2OH), Rt 11.57 minutes.

Provenance & Evidence