Dimethyl Sulfoxide → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 419345Notes

Reaction equation

HRID 419345 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][OH:25])[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(Cl)Cl.C(OCC)C>[CH:24]([CH:21]1[CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19][CH2:20]1)=[O:25]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (18.5 mL, 2M in DCM, 37.0 mmol) in DCM (230 mL) was cooled with a dry ice/acetone bath. DMSO (5.15 mL, 72.6 mmol) was added dropwise via addition funnel and the reaction was stirred for 10 min. N-Boc-4-piperidinemethanol in DCM (20 mL) was added dropwise via addition funnel and the reaction was stirred for 15 min. TEA (17.0 mL, 122 mmol) was then added dropwise via addition funnel and the reaction was warmed to rt. The reaction was diluted with diethyl ether, washed with H2O and brine, dried (MgSO4) and concentrated to provide the title compound (5.36 g, 25.1 mmol, 100%, approximately 96% pure, used without further purification). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29-1.34 (m, 3H), 1.37 (s, 9H), 1.75-1.83 (m, 2H), 2.87 (s, 2H), 3.78 (d, J=13.2 Hz, 2H), 9.56 (s, 1H).

Workup

  1. stirringthe reaction was stirred for 15 min
  2. washwashed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c913435c46a241ed875f145881d81b61
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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