Dimethyl Sulfoxide → HCID 86669385, compound

HRID 537370Notes

Reaction equation

HRID 537370 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:16][CH2:15][N:14]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].CCN(CC)CC>C(Cl)Cl>[CH:12]([CH:13]1[CH2:18][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:16][CH2:15][N:14]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67111267HCID 67111267, compound

Product 1

HCID 86669385HCID 86669385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −78° C., to a solution of Oxalyl Chloride (0.24 mL, 2.75 mmol) in DCM (4 mL), DMSO (0.43 mL, 6.04 mmol) was added. The reaction solution was stirred at the same temperature for 30 min and then a solution of tert-butyl 2-(hydroxymethyl)-4-(2-methoxyphenyl)piperidine-1-carboxylate 125 (580 mg, 1.8 mmol) in DCM (2 mL) was added. The reaction mixture was stirred at −78° C. for 30 min, followed by the addition of Et3N (1.1 mL, 7.32 mmol). The reaction mixture was warmed up to r.t overnight. The reaction was quenched with water and the mixture was extracted with ethyl acetate. After removal of solvent, the crude product of tert-butyl 2-formyl-4-(2-methoxyphenyl)piperidine-1-carboxylate 126 was obtained without further purification. LC/MS RT (5 min method)=2.406 min. Mass observed: 264.1 (M-Buthyl+H).

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 30 min
  2. temperatureThe reaction mixture was warmed up
  3. waitto r.t overnight
  4. customThe reaction was quenched with water
  5. extractionthe mixture was extracted with ethyl acetate
  6. customAfter removal of solvent

Sources & evidence

ORD record
ord-9ed6c79195334e1bb06f3ab5192dd029
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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