Dimethyl Sulfoxide → tert-Butyl 3-(3-oxopropyl)piperidine-1-carboxylate

Temperature

-60 °C

An oven-dried 3-neck 1 L round-bottom flask under nitrogen was charged with DCM (100 mL) and oxalyl chloride (1.98 mL, 22.6 mmol) and cooled to −60° C. DMSO (3.21 mL, 45.2 mmol) was added dropwise, and the reaction mixture was stirred for 5 min. A solution of tert-butyl 3-(3-hydroxypropyl)piperidine-1-carboxylate (5.00 g, 20.6 mmol) in DCM (100 mL) was added via addition funnel, and the reaction mixture was stirred for 20 min. TEA (14.3 mL, 103 mmol) was added, and the reaction mixture was warmed slowly to RT. The reaction mixture was poured into 2.5% NaHCO3 and extracted with methylene chloride. The combined organic layers were washed with 5% KHSO4 then brine, dried with anhydrous MgSO4, filtered and concentrated. The product was purified by silica gel chromatography (80 hexane/20 EtOAc). LRMS (M+H)+=242.3.

1. stirringthe reaction mixture was stirred for 20 min
2. temperaturethe reaction mixture was warmed slowly to RT
3. extractionextracted with methylene chloride
4. washThe combined organic layers were washed with 5% KHSO4
5. dry with materialbrine, dried with anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe product was purified by silica gel chromatography (80 hexane/20 EtOAc)

ORD record

ord-2b67265d443749d09c385701b10ffb6d

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08591878B2