Hydrochloric Acid → HCID 11651444, compound

Participants

Reaction Conditions

Reaction Steps

(R,E)-N-(2,2-dimethylcyclopentylidene)-1-phenylethanamine (4.61 g, 21.4 mmol) in ethanol (50 mL) was cooled to −78° C. and sodium borohydride (0.41 g, 10.7 mmol) was added and the resulting mixture was allowed to stir at −78° C. for 2 h. At this time, the mixture was slowly treated with 6 N aq HCl (15 mL) followed by warming to rt with vigorous stirring. The organics were removed under vacuum and the remaining aqueous portion was cooled and made basic by addition of 10% aq sodium carbonate and the mixture was then extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine, dried over anhyd. sodium sulfate and the organic was decanted and concentrated on rotovap to yield a yellow liquid as the crude product. This material was purified by flash chromatography on silica gel using ethyl acetate/hexanes mixture as the eluent to afford 3.50 g (75%) of the title compound as a clear oil. HPLC (condition B): retention time=1.90 min. LCMS (condition E): m/z 218+ve. 1H NMR (400 MHz, MeOD) δ 7.29-7.41 (4 H, m), 7.20-7.29 (1 H, m), 3.90 (1 H, q, J=6.60 Hz), 2.59 (1 H, dd, J=9.46, 7.92 Hz), 1.66-1.81 (1 H, m), 1.51-1.67 (1 H, m), 1.38-1.50 (3 H, m), 1.37 (3 H, d, J=6.60 Hz), 1.24-1.36 (1 H, m), 1.05 (3 H, s), 0.92 (3 H, s).

Provenance & Evidence