Dimethyl Sulfoxide → 1-Boc-piperidine-3-carboxaldehyde

HRID 2212080Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:24][OH:25])[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][CH2:21][CH:20]([CH:24]=[O:25])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

Dimethylsulphoxide (1.35 ml, 18.8 mmol) was added dropwise to a solution of oxalyl chloride (1.65 ml, 18.8 mmol) in dichloromethane (20 ml) at −78° C. When the addition was complete, the reaction was stirred for a further 15 minutes at −78° C. 1-(tert-Butoxycarbonyl)-3-(hydroxymethyl)piperidine (2.7 g, 12.6 mmol) was added and the reaction warmed to −20° C. and stirred at this temperature for 20 minutes. Triethylamine (5.25 ml, 37.6 mmol) was added and the reaction allowed to warm to room temperature and stirred for 1 hour. The mixture was diluted with dichloromethane and washed with water (×2). The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was taken up in tetrahydrofuran and filtered through cotton wool. The filtrate was evaporated in vacuo to give the title compound (2.32 g, 89%).

Workup

additionWhen the addition
temperaturethe reaction warmed to −20° C.
stirringstirred at this temperature for 20 minutes
temperatureto warm to room temperature
stirringstirred for 1 hour
washwashed with water (×2)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated in vacuo
filtrationfiltered through cotton wool
customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record: ord-897e284f0a54438eb9c3a10c16199d1b
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101892B2

Reaction notes

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