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

HRID 129508

反応式

HRID 129508 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 5612031-N-Cbz-3-pyrrolidinone

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ea7c1b7701d14646b5be5ae07b542132
出典データセット
uspto-grants-1995_11
特許番号
US05468740

関連ノート

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