Hydrochloric Acid → HCID 54451470, compound

Participants

Reaction Steps

Sodium borohydride (423 mg, 11 mol) was added portion-wise over 20 minutes at room temperature, under nitrogen, to a stirred solution of the title compound of Example 37 (1.34 g, 5 mmol) in ethanol (50 ml), then stirring continued for 18 hours. The pH of the resulting reaction mixture was adjusted to 2 with 2N hydrochloric acid, then to 8 with solid sodium carbonate, and the volume reduced to about half by evaporation under reduced pressure, before partitioning between ethyl acetate and water was effected. The organic phase was separated, washed with water, dried (Na2SO4) and evaporated under reduced pressure to give a foam which was purified by column chromatography on silica gel, eluting with a solvent gradient of 0.880 aqueous ammonia:methanol:dichloromethane (0:0:100 to 0:10:90 to 1:10:90 to 1.5:15:85), to afford the title compound as a foam. Rf 0.10 (SS 7). [α]D25 -22° (c=0.1, CH3OH). Found: C,72.07; H,8.96; N,9.56. C17H24N2O; 0.10 CH2Cl2 ; 0.17 H2O requires C,72.34; H,8.71; N,9.87%.

Provenance & Evidence