Dimethyl Sulfoxide → Benzyl 3-formylpyrrolidine-1-carboxylate

HRID 1817663노트

반응식

HRID 1817663 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 4620242Benzyl 3-formylpyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-2575e3412ca44fecb32976cab6fc972d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598257B2

반응 노트

불러오는 중…