Methyl (methylsulfinyl)methyl sulfide → 1-p-Nitrobenzyloxycarbonyl-4-hydroxy-4-methylsulfinylmethylthiomethylpiperidine

To methyl methylthiomethyl sulfoxide (2.23 g) in dry tetrahydrofuran (10 ml) was added dropwise n-butyl lithium (1.15 g) in dry hexane (11.6 ml) at -60° to -70° C. under nitrogen atmosphere and the mixture was stirred for 20 minutes at the same temperature. Subsequently, 1-p-nitrobenzyloxycarbonyl-4-piperidone (5.0 g) in dry tetrahydrofuran (30 ml) was added dropwise thereto at -55° to -70° C. under nitrogen atmosphere. The reaction mixture was diluted with dichloromethane (200 ml) and water (215 ml), warmed slowly to room temperature, dried over anhydrous sodium sulfate and evaporated to give an oily residue which was then purified by silica gel chromatography to give 1-p-nitrobenzyloxycarbonyl-4-hydroxy-4-methylsulfinylmethylthiomethylpiperidine.

1. customat -55° to -70° C.
2. dry with materialdried over anhydrous sodium sulfate
3. customevaporated
4. customto give an oily residue which
5. customwas then purified by silica gel chromatography

ORD record

ord-f2e618b6c3ab4ebdb1878a655134e8a7

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04742052