Dimethyl Sulfoxide → 1-(2,2-Dimethylpropyl)piperidine-4-carbaldehyde

HRID 12398Notes

Reaction equation

HRID 12398 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][OH:23])[CH2:18][CH2:17]1)[C:12]([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl>[CH2:11]([N:16]1[CH2:21][CH2:20][CH:19]([CH:22]=[O:23])[CH2:18][CH2:17]1)[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 21060224[1-(2,2-Dimethylpropyl)piperidin-4-yl]methanol

Product 1

HCID 593377161-(2,2-Dimethylpropyl)piperidine-4-carbaldehydeYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (490 μL, 5.6 mmol) in DCM (10 mL) at −78° C. was added DMSO (796 μL, 11.2 mmol) dropwise followed by the addition of a solution of 20b (943 mg, 5.6 mmol) in DCM (2 mL). The mixture was stirred at −78° C. for 30 min and TEA (3.6 mL, 25.5 mmol) was added. The reaction was stirred at −78° C. for 5 min, warmed to rt and stirred at rt for 30 min. The reaction was quenched with water and extracted with DCM. The organic layers were combined and washed with water, dried over magnesium sulfate to give 20c as a yellow semi-solid (880 mg).

Workup

  1. stirringThe reaction was stirred at −78° C. for 5 min
  2. temperaturewarmed to rt
  3. stirringstirred at rt for 30 min
  4. customThe reaction was quenched with water
  5. extractionextracted with DCM
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-68635d8bc43641c59b183e28455d7656
Source dataset
uspto-grants-2010_06
Patent number
US07728008B2

Reaction notes

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