Dimethyl Sulfoxide → HCID 86638695, compound

HRID 1691674Notes

Reaction equation

HRID 1691674 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([C@H:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH2:19][C@@H:18]2[CH2:29][OH:30])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[C:11]1([C@H:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:28])[C:24]([F:26])([F:27])[F:25])[CH2:19][C@@H:18]2[CH:29]=[O:30])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 59178663HCID 59178663, compound

Product 1

HCID 86638695HCID 86638695, compoundYield 110.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 1.37 mL of DMSO in 20 mL of dichloromethane was cooled to −78° C., and added dropwise 0.845 mL of oxalyl chloride (internal temperature −60° C. or lower). After stirring at the same temperature for 20 minutes, a solution of 1.46 g of rel-[(3R,4S)-4-phenyl-1-(trifluoroacetyl)piperidin-3-yl]methanol in 20 mL of dichloromethane was added dropwise thereto, followed by stirring for additional 20 minutes. 4.40 mL of triethylamine was added dropwise thereto, and the reaction temperature was then elevated to −30° C., followed by stirring for additional 15 minutes. To the reaction mixture was added a saturated ammonium chloride solution to stop the reaction, followed by warming to room temperature, and then extraction with chloroform. The organic layer was washed with water, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 1.597 g of rel-(3R,4S)-4-phenyl-1-(trifluoroacetyl)piperidine-3-carbaldehyde as a crude product.

Workup

  1. stirringby stirring for additional 20 minutes
  2. customwas then elevated to −30° C.
  3. stirringby stirring for additional 15 minutes
  4. customthe reaction
  5. extractionextraction with chloroform
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-499cb8444a4242ebac4a60d1fc314f24
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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