Dimethyl Sulfoxide → HCID 18388380, compound

HRID 2296832Notes

Reaction equation

HRID 2296832 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]([F:26])([F:25])[F:24])[CH:20]([CH2:27][OH:28])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl.CCOCC>[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]([F:26])([F:24])[F:25])[CH:20]([CH:27]=[O:28])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18388364[1-Benzyl-4-(trifluoromethyl)pyrrolidin-3-yl]methanol

Product 1

HCID 18388380HCID 18388380, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.98 mL (11.2 mmol) of oxalyl chloride in 30 mL of CH2Cl2 at −78° C. was added 1.6 mL (22.4 mmol) of DMSO and the reaction mixture was stirred for 10 min. To this reaction mixture at −78° C. was added a solution of 1.46 g (5.6 mmol) of 1-benzyl-3-(RS)-hydroxymethyl-4-(RS)-trifluoromethylpyrrolidine in 10 mL of CH2Cl2. After stirring for 10 min. at −78° C., 3.9 mL (28 mmol) of Et3N was added and the reaction was allowed to warm to rt. The reaction mixture was poured into ether and extracted twice with sat'd NaHCO3 solution and once with sat'd NaCl solution. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give 1.46 g of the title compound.

Workup

  1. stirringAfter stirring for 10 min. at −78° C.
  2. extractionextracted twice with sat'd NaHCO3 solution and once with sat'd NaCl solution
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2c59d4715ff842f883213a59238b24b0
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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