Acetic Acid → HCID 68468405, compound

Participants

Reaction Steps

Dissolve (S)-3-(2-Chloro-6-fluoro-benzyl)-4-oxo-4-((4S,5R)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-butyraldehyde (Preparation 85) (0.384 g, 0.825 mmol) in THF (20 mL). Add cyclohexanamine (0.098 g, 0.99 mmol) and AcOH (0.049 g, 0.82 mmol). Stir the mixture for one hour and then add NaBH(OAc)3 (0.262 g, 1.24 mmol). Stir the reaction mixture for 24 hours until LC-MS shows the starting material has been gone. Add water (20 mL) and extract the aqueous with CH2Cl2 (3×50 mL). Combine the organic layers and dry over Na2SO4. Concentrate and purify by chromatography (Silica gel) to afford (S)-3-(2-Chloro-6-fluorobenzyl)-1-cyclohexylpyrrolidin-2-one (0.172 g, 67%). MS (APCI-pos mode) m,/z (rel intensity) 310 (100), 312 (35).

Provenance & Evidence