Dimethyl Sulfoxide → HCID 86638697, compound

HRID 1691677Notes

Reaction equation

HRID 1691677 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=3)=[O:25])[CH2:20][C@@H:19]2[CH2:37][OH:38])=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][CH:28]=3)=[O:25])[CH2:20][C@@H:19]2[CH:37]=[O:38])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 66906274HCID 66906274, compound

Product 1

HCID 86638697HCID 86638697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 0.3 mL of oxalyl chloride in 5 mL of dichloromethane was added dropwise 0.5 mL of DMSO at −78° C., followed by stirring for 10 minutes. To the reaction mixture was added dropwise a solution of 664 mg of 4-(methoxycarbonyl)phenyl rel-(3R,4S)-4-(4-fluorophenyl)-3-(hydroxymethyl)piperidine-1-carboxylate in 5 mL of dichloromethane at −78° C., followed by stirring for 15 min, and a solution of 1.8 mL of diisopropylethylamine in 3 mL of dichloromethane was then added dropwise, followed by elevation to room temperature over 2 hours. The reaction mixture was concentrated under reduced pressure, and to the residue was added diethylether, followed by washing with saturated brine, and drying over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 4-(methoxycarbonyl)phenyl rel-(3R,4S)-4-(4-fluorophenyl)-3-formylpiperidine-1-carboxylate as a crude product. ESI+: 386

Workup

  1. stirringby stirring for 15 min
  2. waitfollowed by elevation to room temperature over 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionto the residue was added diethylether
  5. washby washing with saturated brine
  6. dry with materialdrying over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d06c9704c904dd2bd3ce93f5d206020
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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