Methanol → 2-Amino-4,4,4-trifluorobutan-1-ol

Participants

Reaction Steps

12.9 ml of 2 M of lithium borohydride solution in THF (25.8 mmol, 2.5 equivalents) were initially charged in 20 ml of THF, 6.5 ml of chlorotrimethylsilane (51.1 mmol, 5 equivalents) were added and the mixture was stirred at RT for 5 min. Then 2.0 g of rac-2-amino-4,4,4-trifluorobutanoic acid hydrochloride (10.3 mmol, 1 equivalent) were added in portions and the mixture was stirred at room temperature overnight. Then 20.4 ml of methanol were added dropwise and, on completion of addition, the mixture was concentrated. The residue was admixed with 12 ml of a 20% aqueous potassium hydroxide solution and extracted three times with dichloromethane. The combined organic solutions were dried over sodium sulphate, filtered and concentrated. 1.58 g (96% of theory; 90% purity) of the title compound were obtained.

Provenance & Evidence