Dimethyl Sulfoxide → HCID 86638698, compound

HRID 1691699Notes

Reaction equation

HRID 1691699 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]1([C@H:17]2[C@H:22]([CH2:23][OH:24])[CH2:21][CH2:20][N:19]([C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH2:18]2)[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[C@H:22]([CH:23]=[O:24])[CH2:21][CH2:20][N:19]([C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])[CH2:18]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 87198618HCID 87198618, compound

Product 1

HCID 86638698HCID 86638698, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-30 °C

Procedure

Under an argon atmosphere, to a solution of 1.62 mL of DMSO in 40 mL of dichloromethane cooled in a dry ice-acetone bath was added dropwise 0.996 mL of oxalyl chloride, while keeping the inner temperature at −70° C. or lower. After stirring for 10 minutes, a solution of 1.64 g of rel-[(3R,4R)-3-phenyl-1-(trifluoroacetyl)piperidin-4-yl]methanol in 25 mL of dichloromethane was added dropwise thereto over 20 minutes. After stirring over 10 min while keeping it at −70° C. or lower, 4.77 mL of triethylamine was added dropwise thereto over 15 min, and the reaction system was warmed to −30° C., followed by stirring for 15 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by warming to room temperature. After extraction with chloroform, the organic layer was washed with water, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain rel-(3R,4R)-3-phenyl-1-(trifluoroacetyl)piperidine-4-carbaldehyde as a crude product (as a pale yellow oily substance, 1.78 g).

Workup

  1. customat −70° C.
  2. waitover 20 minutes
  3. stirringAfter stirring over 10 min
  4. customat −70° C.
  5. waitover 15 min
  6. stirringby stirring for 15 minutes
  7. temperatureby warming to room temperature
  8. extractionAfter extraction with chloroform
  9. washthe organic layer was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationAfter filtration
  12. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-95e603075770481dbb0b20c49b05f8b2
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

Loading…