Dichloromethane → Ammonia dichloromethane

Participants

Reaction Steps

A solution of the product of Example 9 (222 mg) ethyl-pyridin-4-ylmethyl-amine (122 mg), and acetic acid (0.06 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 (246 mg). 1H NMR (400 MHz, CDCl3): 8.51 (m, 2H), 7.29 (m, 2H), 7.24 (m, 2H), 6.84 (d, J=8.6 Hz, 2H), 3.98 (t, J=6.3 Hz, 2H), 3.52 (s, 2H), 3.50 (s, 2H), 2.51-2.44 (m, 4H), 2.40 (br, 4H), 1.97 (m, 2H), 1.62-1.55 (m, 4H), 1.47-1.40 (m, 2H), 1.06 (t, J=7.0 Hz, 3H).

Provenance & Evidence