Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (208 mg), methyl-phenethyl-amine (113 mg), and acetic acid (0.05 mL) in DCM (3 mL) was treated with sodium triacetoxyborohydride (290 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and evaporated. Chromatography of the residue (1-5% 2 M methanolic ammonia/DCM) gave the title compound as a colorless oil (300 mg). 1H NMR (400 MHz, CDCl3): 7.30-7.25 (m, 2H), 7.21-7.16 (m, 5H), 6.83 (d, J=8.6 Hz, 2H), 3.99 (t, J=6.3 Hz, 2H), 3.49 (s, 2H), 2.84-2.79 (m, 2H), 2.65-2.62 (m, 2H), 2.51-2.37 (m, 6H), 2.26 (s, 3H), 1.98 (m, 2H), 1.63-1.56 (m, 4H), 1.47-1.40 (m, 2H).

Provenance & Evidence