Dimethyl Sulfoxide → tert-Butyl (3R)-3-formylpiperidine-1-carboxylate

Temperature

-78 °C

To a solution of DMSO (0.73 mL, 10.2 mmol) in CH2Cl2 (30 mL) at −78° C. was added a solution of oxalyl chloride (0.45 mL. 5.1 mmol) in CH2Cl2 (30 mL). The reaction mixture was stirred for 10 min at −78° C. prior to the addition of a solution of (R)-tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate in CH2Cl2 (5 mL). The mixture was stirred for an additional 30 min at −78° C. Et3N (3.2 mL, 23.2 mmol) was then added in one portion and the mixture was stirred for 10 min at −78° C. and another 30 min while warming to rt. The solution is poured in Et2O (50 mL) and Brine (50 mL), separated. The aqueous phase was extracted with Et2O (2×50 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo to afford (R)-tert-butyl 3-formylpiperidine-1-carboxylate which was used in the next step without purification.

1. stirringThe mixture was stirred for an additional 30 min at −78° C
2. stirringthe mixture was stirred for 10 min at −78° C. and another 30 min
3. temperaturewhile warming to rt
4. customBrine (50 mL), separated
5. extractionThe aqueous phase was extracted with Et2O (2×50 mL)
6. dry with materialThe combined organic extracts were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-5df7f345dbeb4313afb000a76b09145b

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999966B2