Dimethyl Sulfoxide → 1-Benzoylpiperidine-4-carbaldehyde

To 1.99 g of dimethyl sulfoxide in 45 ml CH2Cl2 at −78° C. was added 2.16 g of oxalyl chloride. After 10 min, 1.865 g of 4-hydroxymethyl-N-benzoyl piperidine (step B) in 15 ml of CH2Cl2 was added at −78° C. and stirred for 30 min. DIEA (5.49 mL) was added and this mixture was stirred for an additional 30 min. at −78° C. and then warmed to room temperature and stirred another 30 min. The reaction was quenched with 50 mL H2O and extracted with 3×50 ml CH2Cl2. The combined organic layers were dried over MgSO4 and evaporated under reduced pressure. The residue was chromatographed with 2:1 hexane:EtOAc, followed by 1:1 hexane: EtOAc to give 1.445 g of the title compound. 1H NMR (500 MHz) 1.72 (m, 2H), 1.90 (m, 1H), 2.14 (m, 1H), 2.58 (m, 1H), 3.21 (m, 2H), 3.68 (m, 1H), 4.41 (m, 1H), 7.39 (m, 5H), 9.72 (m, 1H).

1. stirringthis mixture was stirred for an additional 30 min. at −78° C.
2. stirringstirred another 30 min
3. customThe reaction was quenched with 50 mL H2O
4. extractionextracted with 3×50 ml CH2Cl2
5. dry with materialThe combined organic layers were dried over MgSO4
6. customevaporated under reduced pressure
7. customThe residue was chromatographed with 2:1 hexane

ORD record

ord-eefc50e3ab8b49e48f42dfca96660a3c

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248755B1