Dimethyl Sulfoxide → Tert-butyl 4,4-difluoro-2-formylpyrrolidine-1-carboxylate

HRID 354398노트

반응식

HRID 354398 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][CH:9]1[CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.CS(C)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([F:13])([F:14])[CH2:10][CH:9]1[CH:15]=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 22001352Tert-butyl 4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 23511694Tert-butyl 4,4-difluoro-2-formylpyrrolidine-1-carboxylate수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred mixture of 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethanol (2.11 g, 8.89 mmol), Et3N (6.2 ml, 44.5 mmol), DMSO (6.3 ml, 88.9 mmol) in CH2Cl2 (20 ml) was added SO3-pyridine (4.25 g, 26.7 mmol). After 3 h stirring, the mixture was concentrated in vacuo and diluted with Et2O (200 ml). The resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml), dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give 1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinecarbaldehyde (1.40 g, 67%) as a yellow oil. 1H-NMR (CDCl3) δ1.45-1.52 (m, 9 H), 2.49 (m, 2 H), 3.75-3.88 (m, 2 H), 4.29-4.42 (m, 1 H), 9.54 and 9.60 (s, each, total 1 H).

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. additiondiluted with Et2O (200 ml)
  3. washThe resulting mixture was washed with 1 N HCl (100 ml) and brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent

출처 및 근거

ORD 기록
ord-e5557662dca544ac8e5c4666f7854951
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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