Imidazole → (S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-one

HRID 2279467노트

반응식

HRID 2279467 반응식
[OH:1][C@@H:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Si:20]([O:1][C@@H:2]([CH3:10])[C:3]([N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 11051776(2S)-2-hydroxy-1-(1-pyrrolidinyl)-1-propanone

생성물 1

HCID 11807344(S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-one수율 77.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 108 (41.1 g, 287.0 mmol), imidazole (29.31 g, 430.6 mmol), and DMAP (3.507 g, 28.70 mmol) in DMF (100 mL) was added slowly tert-butylchlorodimethylsilane (54.08 g, 358.8 mmol) and the reaction was stirred at RT for 18 h. Water was added and mixture was extracted with Et2O. The organic layer was dried, filtered, and concentrated. The resulting residue was purified by passing through a SiO2 plug eluting with an EtOAc/hexane gradient (10 to 50% EtOAc) to afford 56.93 g (77.04%) of (S)-2-(tert-butyldimethylsilyloxy)-1-(pyrrolidin-1-yl)propan-1-one (110).

후처리

  1. extractionmixture was extracted with Et2O
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified
  6. washeluting with an EtOAc/hexane gradient (10 to 50% EtOAc)

출처 및 근거

ORD 기록
ord-2924cbacd0714900949f796d8899a9d2
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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