Diisopropylethylamine → Ethyl acetate hexane

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-4-benzyl-3-(2-(3-fluoro-4-(trifluoromethyl)phenyl)acetyl)oxazolidin-2-one (1.6 g, 4.20 mmol) was dissolved in dichloromethane (40 mL), cooled to −78° C. and treated slowly with titanium (IV) chloride (4.4 mL, 4.40 mmol). This was followed by treatment with diisopropylethylamine (0.76 mL, 4.36 mmol). The mixture was stirred at −78° C. for 15 minutes, and tert-butyl 2-methoxypyrrolidine-1-carboxylate (1.0 g, 4.97 mmol) was added. After 15 minutes, the reaction was allowed to warm to ambient temperature for one hour. The reaction was quenched with saturated NH4Cl (20 mL) and extracted with dichloromethane (3×100 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate (4:1), (1.44 g, 62.3% yield). 7.55 (t, J=8.2, 1H), 7.38-7.18 (m, 7H), 5.61-5.51 (m, 1H), 4.72-4.56 (m, 2H), 4.16-4.02 (m, 2H), 3.43-3.34 (m, 1H), 3.28-3.15 (m, 1H), 2.77-2.61 (m, 1H), 1.96-1.80 (m, 1H), 1.75-1.56 (m, 4H), 1.48 (s, 9H).

Provenance & Evidence