Diethyl Ether → HCID 11573330, compound

Participants

Reaction Conditions

Reaction Steps

Dibal-H (7.08 mL, 7.08 mmol) was added as a 1.0 N solution in CH2CL2 at −78° C. to crude ethyl N-benzyl-N-(3-chloro-4-fluorophenyl)valinate (8-2, 0.322 g, 0.885 mmol). The mixture stirred for 5 h as it warmed to 23° C. Diethyl ether (40 mL) and H2O (1.2 mL) were added and mixture continued stirring for 20 min before filtering. The filtrate was concentrated and purified by reverse-phase liquid chromatography (Semi Prep YMC C-18 Reverse Phase Column 5% CH3CN/H2O to 95% CH3CN/H2O with 0.1% TFA present) to provide 2-[benzyl(3-chloro-4-fluorophenyl)amino]-3-methylbutan-1-ol (8-3) as a brown oil. 1H NMR (300 MHz, CDCl3) 7.37-7.171 (m, 5H), 6.92-6.86 (m, 2H), 6.67 (ddd, J=9.16, 3.35, 3.35 Hz, 1H), 4.45 (s, 2H), 3.91-3.87 (m, 1H), 3.68-3.55 (m, 2H), 2.04-1.92 (m, 1 μl), 1.70 (brs, 1H), 1.00 (d, J=6.72 Hz, 3H), 0.91 (d, J=6.71, 3H).

Provenance & Evidence