Imidazole → (3R,4S)-3-[4-(4-Bromophenoxy)-3-(t-butyldimethylsilanyloxy)hexyl]pyridine

HRID 380052노트

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HRID 380052 반응식
[Br:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@@H:7]([CH2:18][CH3:19])[C@H:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[C:22]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23].N1C=CN=C1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]([CH2:18][CH3:19])[C@H:8]([O:17][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:20][CH:21]=1

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57271083(3r,4s)-4-(4-Bromophenoxy)-1-pyridin-3-yl-hexan-3-ol

생성물 1

HCID 57090865(3R,4S)-3-[4-(4-Bromophenoxy)-3-(t-butyldimethylsilanyloxy)hexyl]pyridine수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of (3R,4S)-4-(4-bromophenoxy)-1-pyridin-3-yl-hexan-3-ol (1.34 g, Example 87d)) in dry N,N-dimethylformamide (30 ml) was added tertbutyldimethylsilyl chloride (0.80 g) and imidazole (0.77 g) and the resulting solution heated at 50° C. for 20 hours. The solution was concentrated in vacuo. The residue was made basic by addition of saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate:isohexane (1:1) to give the sub-title compound as an oil (0.71 g).

후처리

  1. concentrationThe solution was concentrated in vacuo
  2. additionThe residue was made basic by addition of saturated sodium hydrogen carbonate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with ethyl acetate:isohexane (1:1)

출처 및 근거

ORD 기록
ord-8f101bee1e1445f181fbec58fa541093
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300352B1

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