Pyridine → N-[(1Z)-{(E,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-2-oxoindene-3-ylidene}methyl]-N-phenethylacetamide

HRID 1922638노트

반응식

HRID 1922638 반응식
[Br:1]/[CH:2]=[C:3]1/[C@H:4]2[C@:8]([CH3:12])([CH2:9][CH2:10][CH2:11]/1)/[C:7](=[CH:13]/[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:6](=[O:21])[CH2:5]2.[C:22](Cl)(=[O:24])[CH3:23].N1C=CC=[CH:28][CH:27]=1>>[Br:1]/[CH:2]=[C:3]1\[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[C@H:4]\1[CH2:5][C:6](=[O:21])/[C:7]/2=[CH:13]\[N:14]([CH2:15][CH2:16][C:17]1[CH:28]=[CH:27][CH:20]=[CH:19][CH:18]=1)[C:22](=[O:24])[CH3:23]

참가 물질

4

반응물 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 67493986(1Z,3aR,4E,7aS)-4-(bromomethylene)-hexahydro-7a-methyl-1-{(phenylamino)methylene}-1H-indene-2(3H)-one2회

생성물 1

HCID 59456519N-[(1Z)-{(E,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-2-oxoindene-3-ylidene}methyl]-N-phenethylacetamide수율 91%

실험 절차

To a solution of (1Z,3aR,4E,7aS)-4-(bromomethylene)-hexahydro-7a-methyl-1-{(phenylamino)methylene}-1H-indene-2(3H)-one (Compound 27: 182 mg, 0.486 mmol) in pyridine (1 ml), acetyl chloride (50 μl, 0.703 mmol) was added at 0° C. The resulting mixture was allowed to rise to room temperature and stirred for 30 minutes. The solvent was removed by evaporator, and the residue was dissolved in diethyl ether. The resulting mixture was washed with 2 N hydrochloric acid, water and with saturated brine, and dried over magnesium sulfate, followed by evaporation under reduced pressure to obtain a crude product of N-[(1Z)-{(E,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-2-oxoindene-3-ylidene}methyl]-N-phenethylacetamide (184 mg, 91%).

후처리

  1. customto rise to room temperature
  2. customThe solvent was removed by evaporator
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe resulting mixture was washed with 2 N hydrochloric acid, water and with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customfollowed by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-e3c2656129154a0e9a6eaa48550227b4
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173824B2

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