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Water → N-(3-{6-Methyl-3-[(E)-3-(3-thienyl)-2-propenyl]-3-azabicyclo[3.1.0]hex-6-yl]phenyl)methanesulfonamide

HRID 1826391
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HRID 1826391 반응식
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH3:5].[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[CH2:6]2
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참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226445Aluminium lithium hydrideHCID 22141215N-(3-{6-methyl-3-[(E)-3-(3-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

생성물 2

HCID 222AmmoniaHCID 22141277
N-(3-{6-Methyl-3-[(E)-3-(3-thienyl)-2-propenyl]-3-azabicyclo[3.1.0]hex-6-yl]phenyl)methanesulfonamide
수율 66.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-(3-{6-methyl-3-[(E)-3-(3-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 132, 100 mg, 0.248 mmol) in anhydrous tetrahydrofuran (2.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.25 ml, 0.25 mmol) and the reaction mixture was stirred at room temperature for 7 h. The rapidly stirred reaction mixture was treated sequentially with water (0.25 ml), sodium carbonate (250 mg) and ethyl acetate (2.5 ml). The reaction mixture was left to stir overnight and then was filtered and concentrated in vacuo. This was purified by chromatography using silica gel (2 g) eluting with ethyl acetate:hexane:0.880 ammonia (60:40:1) to afford the title compound as a colourless oil (32 mg, 33%).

후처리

  1. customThe rapidly stirred reaction mixture
  2. waitThe reaction mixture was left
  3. stirringto stir overnight
  4. filtrationwas filtered
  5. concentrationconcentrated in vacuo
  6. customThis was purified by chromatography
  7. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-2bddffe8ca764e6db1b4d2839b6eb4a6
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07049444B2

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