2-(Methylamino)ethanol → HCID 71238254, compound

Participants

Reaction Steps

To a solution of 39 (600 mg, 2.0 mmol) in THF (25 mL) was added 2-(methyl amino) ethanol (224 mg, 3.0 mmol) and a catalytic amount of acetic acid (0.1 mL) and cooled to 0° C. Na(OAc)3BH (1 g, 5.0 mmol) was added portion wise and the reaction mixture allowed to warm and stired at rt for 3 h. The reaction mixture was neutralized by using NaHCO3 (aq), diluted with water (25 mL, 1:3 dilution), extracted with EtOAc (2×100 mL), the combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated. The crude compound was purified by column chromatography (neutral alumina, eluted with 5% MeOH/CHCl3) to obtain compound 40 (400 mg, 55%) as a brown solid. Rf: 0.3 (10% MeOH/CHCl3); (m/z): 362 [MH]+; 1H NMR (400 MHz, DMSO-d6) δ 7.91 (1H, d, J=2.8 Hz), 7.35-7.22 (10H, m), 7.12 (1H, d, J=8.8 Hz), 7.02 (1H, dd, J=2.8, 8.8 Hz), 4.72 (4H, s), 4.37 (1H, br s), 3.46-3.44 (4H, m), 2.40 (2H, t, J=6.4 Hz), 2.13 (3H, S).

Provenance & Evidence