Dimethyl Sulfoxide → HCID 59438420, compound

HRID 2177476Notes

Reaction equation

HRID 2177476 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH:23]([OH:27])[CH:22]1[CH3:28])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.O>[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH:22]1[CH3:28])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 594384841236302-37-6

Product 1

HCID 59438420HCID 59438420, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 309.5 ul (3.530 mmol) oxalyl chloride in 3 ml dichloromethane at −50° C. to −60° C. was added a solution of 873 ul DMSO in 2 ml dichloromethane. The reaction mixture was stirred for 10 minutes, after which a solution of 800 mg (3.209 mmol) 3-hydroxy-2-methyl-piperidine-1-carboxylic acid benzyl ester in 3 ml dichloromethane was added over a period of 10 minutes. Stirring was continued for an additional 30 minutes. To this, was subsequently added 2.24 ml (16.05 mmol) triethylamine. The reaction mixture was stirred for 15 minutes, then allowed to warm to room temperature, taken in water, separated, and the aqueous layer extracted with dichloromethane. The combined organic layers were washed twice with water, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 40) to provide 600 mg (76%) of the title compound as a light yellow oil. MS (m/e): 270.2 (M+Na+).

Workup

  1. stirringStirring
  2. waitwas continued for an additional 30 minutes
  3. stirringThe reaction mixture was stirred for 15 minutes
  4. customseparated
  5. extractionthe aqueous layer extracted with dichloromethane
  6. washThe combined organic layers were washed twice with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified with flash column chromatography on silica gel (Eluent: Heptane/ethyl acetate 0 to 40)

Sources & evidence

ORD record
ord-a6875007d7084d4b8ec16a0c39077075
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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