Water → 6-(3-Nitrophenyl)-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hexan-2-one

HRID 1826418노트

반응식

HRID 1826418 반응식
Br[CH2:2][CH:3]1[CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[CH:4]1[C:15]([O:17]CC)=O.C(=O)([O-])O.[Na+].[C:25]1([CH2:31][CH2:32][CH2:33][NH2:34])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C)C=O>[N+:12]([C:8]1[CH:7]=[C:6]([CH:5]2[CH:4]3[CH:3]2[CH2:2][N:34]([CH2:33][CH2:32][CH2:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]3=[O:17])[CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 162593-PhenylpropylamineHCID 516892Sodium BicarbonateHCID 22141287Ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane Carboxylate

생성물 1

HCID 221413026-(3-Nitrophenyl)-3-(3-phenylpropyl)-3-azabicyclo[3.1.0]hexan-2-one수율 90.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

To a solution of ethyl 2-(bromomethyl)-3-(3-nitrophenyl)cyclopropane carboxylate (Preparation 23, 60 mg, 0.18 mmol) in N,N-dimethylformamide (2 ml) was added sodium hydrogen carbonate (30 mg, 0.36 mmol) and 3-phenylpropylamine (30 mg, 31 μl, 0.22 mmol). The mixture was heated to 150° C. for 1 hour, then cooled to room temperature and stirred for 16 hours. Water (30 ml) was added and the mixture was extracted with diethyl ether (2×50 ml). The combined extracts were concentrated in vacuo and the residue was purified by silica (5 g) column chromatography eluting with dichloromethane then 4:1 dichloromethane:ethyl acetate. Product-containing fractions were combined and concentrated in vacuo to give the title compound as a colourless glassy solid (55 mg, 90%).

후처리

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with diethyl ether (2×50 ml)
  3. concentrationThe combined extracts were concentrated in vacuo
  4. customthe residue was purified by silica (5 g) column chromatography
  5. washeluting with dichloromethane
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e6c75fc90fc24182bed9d92b94dc8b68
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049444B2

반응 노트

불러오는 중…