Dimethyl Sulfoxide → 1-N-Cbz-3-pyrrolidinone

HRID 1588353Notes

Reaction equation

HRID 1588353 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]([N:21]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>O>[CH2:11]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 5612031-N-Cbz-3-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150 ml of oxalic acid chloride was added to 2 liters of dichloromethylene. 245 ml of dimethylsulfoxide was gradually added at -70° to -50° C. in a stream of argon. 70.67 g of N-(N-(benzyloxycarbonyl)-3-pyrrolidinol dissolved in dichloromethylene was dropped. After gradual dropping of 720 ml of triethylamine, the mixture was raised to room temperature. After completion of the reaction, the reaction solution was poured into water and extracted with dichloromethylene, followed by removal of the solvent by distillation under reduced pressure. The residue was purified by column chromatography (eluting solvent: hexane-ethyl acetate), thereby obtaining 66.55 g of the intended compound.

Workup

  1. additionwas dropped
  2. customAfter completion of the reaction
  3. extractionextracted with dichloromethylene
  4. customfollowed by removal of the solvent by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluting solvent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9a7a675a172e4070abf3191d5d0c0ad0
Source dataset
uspto-grants-1993_06
Patent number
US05221671

Reaction notes

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