Dimethyl Sulfoxide → Tert-butyl 4-(3-oxopropyl)piperidine-1-carboxylate
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][OH:27])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH:26]=[O:27])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of oxalyl chloride (2 mL, 22 mmol) in dry dichloromethane (50 mL) at −78° C. under argon, was added dropwise a solution of dimethylsulfoxide (3.4 mL, 44 mmol) in dichloromethane (10 mL). After 2 min, a solution of 3-[N-(t-butoxycarbonyl)piperidin-4-yl]propanol (4.86 g, 20 mmol) in dichloromethane (10 mL) was added dropwise over 5 min. After stirring an additional 15 min at −78° C., triethylamine (14 mL) was added dropwise. After 5 min, the reaction became a thick white slurry and was allowed to warm to RT and stirred for 16 h. The reaction mixture was washed with cold 1N hydrochloric acid and with brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane) to yield the title compound (4.18 g, 87%). TLC Rf 0.40 (30% ethyl acetate/hexane); 1H NMR (CDCl3) δ0.95-1.80 (7H, m), 1.48 (9H, s), 2.40-2.90 (4H, m), 4.14 (2H, br dt), 9.88 (1H, t).
Workup
- waitAfter 5 min
- temperatureto warm to RT
- stirringstirred for 16 h
- washThe reaction mixture was washed with cold 1N hydrochloric acid and with brine
- dry with materialdried (magnesium sulfate)
- concentrationconcentrated
- customThe residue was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-65a4744c7ac8478ca6f5aee02191ff3c
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403578B1
Reaction notes
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