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

HRID 1642112Notes

Reaction equation

HRID 1642112 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=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(N(CC)CC)C.[NH4+].[Cl-]>C(Cl)Cl>[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

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

DMSO (2.2 equivalents) was added at −78° C., under an inert gas atmosphere, to a solution of oxalyl chloride (1.1 equivalents) in dry CH2Cl2, and stirring was carried out for 1 h. A solution of N-Boc-4-piperidinemethanol (1 equivalent) in dry DCM was added dropwise to the reaction mixture at −70° C., and stirring was carried out for 2 h. After addition of triethylamine (2.5 equivalents), the reaction solution was allowed to warm to RT, and saturated aqueous NH4Cl solution and DCM were added thereto. The organic phase was separated and washed with water and saturated aqueous NaCl solution. After drying the organic phase over Na2SO4 and filtration, the solvent was removed in vacuo. The product was used in the next stage without being purified further.

Workup

  1. stirringstirring
  2. waitwas carried out for 2 h
  3. customThe organic phase was separated
  4. washwashed with water and saturated aqueous NaCl solution
  5. customAfter drying the organic phase
  6. filtrationover Na2SO4 and filtration
  7. customthe solvent was removed in vacuo
  8. customwithout being purified further

Sources & evidence

ORD record
ord-6ef9a3dc4a1047a98f41f9f15e11ee45
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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