Dimethyl Sulfoxide → tert-Butyl 4-formylpiperidine-1-carboxylate

Temperature

25 °C

A mixture of dry DMSO (223.26 mmol, 4.0 eq.) and dry methylene chlloride (100 ml) was added dropwise to a solution of oxalyl chloride (111.63 mmol, 2.0 eq.) in dry methylene chloride (100 ml) at −78° C. A solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (55.81 mmol, 1.0 eq.) in dry methylene chloride (100 ml) was added dropwise to the reaction mixture at same temperature and it was then stirred for 30 min. Et3N (279.07 mmol, 5.0 eq.) was added at −78° C. and the reaction mixture allowed to slowly warm to 25° C. and stir for another 30 min. The reaction mixture was quenched with saturated ammonium chloride solution (200 ml), diluted with methylene chloride (100 ml) and the layers were separated. The organic layer was washed with brine (200 ml) and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the crude desired product as light orange oil which is used in the next step without purification. Yield: 95%

1. stirringstir for another 30 min
2. customThe reaction mixture was quenched with saturated ammonium chloride solution (200 ml)
3. additiondiluted with methylene chloride (100 ml)
4. customthe layers were separated
5. washThe organic layer was washed with brine (200 ml)
6. dry with materialdried over sodium sulfate
7. customThe solvent was evaporated under reduced pressure

ORD record

ord-8b35d88a9a6144a68f303303ec29001d

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08455475B2