Sodium Hydroxide → HCID 69416326, compound

Participants

Reaction Conditions

Reaction Steps

(4S)-7-Chloro-4-methyl-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole (0.152 g; 0.689 mmol) is dissolved in a tetrahydrofurane/trifluoroacetic acid mixture (1:2; 7.5 ml) and cooled to 0° C. Sodium borohydride (52 mg; 1.38 mmol) is added and the solution was stirred for 2 h. The reaction mixture was poured in an aqueous NaOH solution (pH was put to 14) and extracted twice with ethyl-acetate. Organic phases were pooled, dried with MgSO4 and the solvent was evaporated. Chromatography on silica gel (dichloromethane/methanol 9:1) gave (4S,10aS)-7-Chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (113 mg, 74%) and (4S,10aR)-7-Chloro-4-methyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indole (12 mg, 8%).

Provenance & Evidence