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Water → (R)-N-(5-(1,2-Dihydroxy-ethyl)-pyrdin-2-yl)-2,2-dimethylpropionamide

HRID 1596499
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HRID 1596499 반응식
C([OH:5])(C)(C)C.[CH:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=1)=[CH2:7].S([O-])([O-])=O.[Na+].[Na+].[OH2:27]>>[OH:27][C@H:6]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][CH:13]=1)[CH2:7][OH:5]
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참가 물질

5

반응물 4

HCID 962WaterHCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 217020792,2-Dimethyl-N-(5-vinylpyridin-2-yl)-propionamide

생성물 1

HCID 15540846(R)-N-(5-(1,2-Dihydroxy-ethyl)-pyrdin-2-yl)-2,2-dimethylpropionamide수율 96%

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온도
5 °C

실험 절차

A suspension of AD-Mix-B® (1.40 g) in water (5 ml) and t-butanol (5 ml) was cooled to 5° C. and N-(5-vinyl-pyridin-2-yl)-2,2-dimethylpropionamide (0.204 g, 1.0 mmol) was added. The mixture was stirred at 5° C. for 18 hours. The reaction mixture was then treated with sodium sulfite (3.0 g), stirred for 30 minutes and then extracted with dichloromethane. The dichloromethane extract was washed with water and brine and then dried and evaporated to afford 0.230 g (96%) of the title product as colorless crystals. mp 105-106° C. 1H NMR (CDCl3): δ=8.21 (br, 1 H); 8.10 (m, 2 H); 7.61 (d of d, 1 H); 4.70 (m, 1 H); 3.64 (m, 1 H); 3.57 (m, 1 H); 1.25 (s, 9 H). MS (Cl): m/z=239 (M+H+).

후처리

  1. stirringstirred for 30 minutes
  2. extractionextracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with water and brine
  5. customdried
  6. customevaporated

출처 및 근거

ORD 기록
ord-da8f4d6ee55c4ce79dccdf2e4a2aee17
출처 데이터셋
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06291489B1

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