Sodium Thiosulfate → (3R,5R,6S)-1-((S)-1-(tert-Butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidine-3-carbaldehyde

Participants

Reaction Steps

To a stirred solution of (3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-(hydroxymethyl)-3-methylpiperidin-2-one (210 mg, 0.311 mmol; Example 248, Step B) in CH2Cl2 (8 mL) at 0° C. was added NaHCO3 (131 mg, 1.56 mmol) and Dess Martin periodinane (158 mg, 0.373 mmol) in one portion. The reaction was stirred at rt for 2 hours. The reaction was diluted with CH2Cl2 (30 mL) and treated with Na2S2O3 (15 mL, saturated aqueous solution) and NaHCO3 (15 mL, saturated aqueous solution) at rt for 2 hours. The separated aqueous layer was extracted with CH2Cl2 (2×50 mL) and the combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo to give the title compound. Mass Spectrum (ESI) m/z=672.2 (M+1).

Provenance & Evidence