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Butyl bromide → (6-Butoxy-pyridin-3-yl)-(S)(+)-(2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

HRID 552585
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HRID 552585 반응식
[OH:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:9])=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(Cl)Cl>[CH2:22]([O:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:9])=[CH:4][CH:3]=1)[CH2:23][CH2:24][CH3:25]
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참가 물질

6

반응물 3

HCID 8002Butyl bromideHCID 10796Cesium carbonateHCID 178519724(6-Hydroxy-pyridin-3-yl)-(S)(+)-(2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone

생성물 1

HCID 11960840(6-Butoxy-pyridin-3-yl)-(S)(+)-(2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone수율 50.6%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 31275
1,4-Dioxane
용매

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온도
85 °C

실험 절차

A mixture of (6-hydroxy-pyridin-3-yl)-(S)(+)-(2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-methanone (85 mg, 0.31 mmol), 1-bromo butane (0.04 mL, 0.36 mmol), cesium carbonate (195 mg, 0.60 mmol), and catalytic KI in dioxane (5 mL) is stirred under nitrogen at 80-90° C. for 10 h. The reaction is diluted with CH2Cl2, filtered, and washed with brine. The organic portion is dried over Na2SO4, filtered and evaporated. The crude product is partially purified by a SCX column (MeOH wash, elution with 2M NH3 in MeOH. Further purification is accomplished using silica-gel column chromatography (gradient: 100% CH2Cl2 to 10% 2M NH3 in MeOH/CH2Cl2) to give the title compound (52 mg, 50%). MS (ES+) 332.2 (M+H)+.

후처리

  1. filtrationfiltered
  2. washwashed with brine
  3. dry with materialThe organic portion is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is partially purified by a SCX column (MeOH
  7. washwash
  8. washelution with 2M NH3 in MeOH
  9. customFurther purification

출처 및 근거

ORD 기록
ord-0277d172b47b4672af4557fc45a2b3b5
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951826B2

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