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

Temperature

-78 °C

To a solution of 1.75 mL (20 mmol) of oxalyl chloride in 20 mL of CH2Cl2 at −78° C. was added a solution of 2.13 mL (30 mmol) of DMSO in 5 mL of CH2Cl2 and the reaction mixture was stirred for 20 min at −78° C. To this reaction mixture was then added a solution of 2.41 g (11.2 mmol) of 1-t-butoxycarbonyl-4-hydroxymethylpiperidine in 10 mL of CH2Cl2. After stittring for 30 min, 7 mL of Et3N was then added and the reaction mixture was allowed to slowly warm to rt and stirred at rt for 1 h. To the reaction mixture was added 50 mL of H2O and the mixture was extracted with CH2Cl2. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was cocentrated give 2.45 g of the title compound which was used without further purification.

1. waitAfter stittring for 30 min
2. temperatureto slowly warm to rt
3. stirringstirred at rt for 1 h
4. extractionthe mixture was extracted with CH2Cl2
5. washThe combined organic fractions were washed with sat'd NaCl solution
6. dry with materialdried over MgSO4
7. filtrationfiltered

ORD record

ord-7b6327f6c86a4bf59657739ad6e78baa

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303593B1