Dimethyl Sulfoxide → HCID 67065856, compound

HRID 241550Notes

Reaction equation

HRID 241550 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:30]1[CH2:34][CH2:33][C@@H:32]([OH:35])[CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[C:11]([N:30]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31]1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58455161HCID 58455161, compound

Product 1

HCID 67065856HCID 67065856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

To a stirred solution of anhydrous dichloromethane (35.0 mL) in a 3-necked flask with a thermometer, oxalyl chloride (1.5 mL) was added and the resulting solution was cooled to −60° C. A solution of dimethyl sulfoxide (2.6 mL) in dichloromethane (7.5 mL) was added over a period of 10 min, and then (3R)-1-tritylpyrrolidin-3-ol (5.0 g) in dichloromethane (15.0 mL) was added over a period of 10 min. The resulting solution was stirred at −60° C. for 15 min., then triethylamine (10.6 mL) was added over a period of 5 min. A white precipitate was formed. After 5 min, the cooling bath was removed and the mixture was allowed to warm to room temperature. Water (45 mL) was added. The mixture was stirred for an additional 30 min and then extracted with dichloromethane. The organic phase was washed with 5% aqueous citric acid solution, dried over anhydrous sodium sulfate, filtered and concentrated to yield the title compound. LC-MS=243.1 (M+1).

Workup

  1. customA white precipitate was formed
  2. waitAfter 5 min
  3. customthe cooling bath was removed
  4. temperatureto warm to room temperature
  5. additionWater (45 mL) was added
  6. stirringThe mixture was stirred for an additional 30 min
  7. extractionextracted with dichloromethane
  8. washThe organic phase was washed with 5% aqueous citric acid solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-668be6e024d84ac9bbdca8fb9eb0f8f3
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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