Dimethyl Sulfoxide → Benzyl 3-formylpyrrolidine-1-carboxylate

HRID 41018ノート

反応式

HRID 41018 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14]1.O>C(Cl)Cl>[CH:12]([CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[CH2:14]1)=[O:11]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 18332648Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

生成物 1

HCID 4620242Benzyl 3-formylpyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

DMSO (597 μL, 8.42 mmol) was added to a solution of oxalyl chloride (427 μL, 5.05 mmol) in DCM (25 mL) at −78° C. After 5 minutes, benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (generated in Step 1) was added. The reaction was continued for 30 minutes at −78° C. TEA (2.3 mL, 17 mmol) was then added. The resulting mixture was then allowed to warm to room temperature over the course of 30 minutes. Water was then added. The layers were separated and the organic phase was washed sequentially with 0.1 N HCl, water, saturated NaHCO3, and brine. The organic phase was then dried over sodium sulfate and the solvent was removed in vacuo to afford the product (0.82 g, 88% over two steps).

後処理

  1. waitThe reaction was continued for 30 minutes at −78° C
  2. customThe layers were separated
  3. washthe organic phase was washed sequentially with 0.1 N HCl, water, saturated NaHCO3, and brine
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customto afford the product (0.82 g, 88% over two steps)

出典と根拠

ORDレコード
ord-5e0b1f53aca24c0aa0fe85932caf779b
出典データセット
uspto-grants-2013_09
特許番号
US08530485B2

反応ノート

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