Dimethyl Sulfoxide → Methyl 4-formylpiperidine-1-carboxylate

Temperature

-10 °C

To a solution of oxalyl chloride (4.1 mL, 8.2 mmol) in dichloromethane (4 mL) at −78° C. was added dropwise a solution of dimethylsulfoxide (1.2 mL, 16.4 mmol) in dichloromethane (4 mL). After stirring for 5 min, a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid methyl ester (1.3 g, 7.5 mmol) in dichloromethane (5 mL) was added. The resulting solution was stirred for another 5 min, then triethylamine (5.2 mL, 37.3 mmol) was added and the mixture allowed to warm to −10° C. After stirring for 1 h, dichloromethane (100 mL) was added, and the organic layer was washed with 1M aqueous phosphoric acid, 1M aqueous sodium hydroxide, and brine. The solution was dried over sodium sulfate then evaporated to afford the title intermediate as a wheat colored oil (1.0 g, 5.8 mmol, 78%). 1H NMR (300 MHz, DMSO-d6): δ (ppm) 1.36 (m, 2H), 1.83 (m, 2H), 2.48 (br m, 1H), 2.93 (br t, 2H), 3.56 (s, 3H), 3.80 (br d, 2H), 9.56 (s, 1H).

1. stirringThe resulting solution was stirred for another 5 min
2. stirringAfter stirring for 1 h
3. washthe organic layer was washed with 1M aqueous phosphoric acid, 1M aqueous sodium hydroxide, and brine
4. dry with materialThe solution was dried over sodium sulfate
5. customthen evaporated

ORD record

ord-a4a6b0167e2349cab102b2401a0997f6

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143279B2