Ethylamine → alpha-(Cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-7-hydroxy-6-methoxy-2(1H)-isoquinolineheptanenitrile

HRID 274021노트

반응식

HRID 274021 반응식
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([S:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:8]#[N:9].CC([Si](C)(C)[O:32][C:33]1[CH:42]=[C:41]2[C:36]([CH2:37][CH2:38][NH:39][CH2:40]2)=[CH:35][C:34]=1[O:43][CH3:44])(C)C.C(N)C>C(#N)C>[CH:21]1([S:20][C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:39]2[CH2:38][CH2:37][C:36]3[C:41](=[CH:42][C:33]([OH:32])=[C:34]([O:43][CH3:44])[CH:35]=3)[CH2:40]2)[C:8]#[N:9])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

참가 물질

5

반응물 3

HCID 6341EthylamineHCID 152855547-[[(1,1-Dimethylethyl)dimethylsily]oxy]-1,2,3,4-tetrahydro-6-methoxyisoquinolineHCID 19042070alpha-(5-Bromopentyl)-alpha-(cyclohexylthio)-3,4-dimethoxybenzeneacetonitrile

생성물 1

HCID 10650088alpha-(Cyclohexylthio)-alpha-(3,4-dimethoxyphenyl)-3,4-dihydro-7-hydroxy-6-methoxy-2(1H)-isoquinolineheptanenitrile수율 150.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture, under argon, of 2.17 g of product from Example 113, 1.8 g of product from Example 28, 13.0 ml of N,N-diidopropyl ethylamine and 80 ml of acetonitrile is heated under reflux temperature for 8 hours. The reaction is cooled and concentrated in vacuo and dried under high vacuum for 1 hour. The crude residue is dissolved in 70 ml of tetrahydrofuran and 10.0 ml of 1M tetrabutyl ammonium fluoride in tetrahydrofuran is added and the mixture is stirred at room temperature, under argon, for 2.5 hours. The mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride, dried, filtered, and concentrated in vacuo to give 4.0 g of a brown oil. The oil is purified by chromatography (silica gel: 1%, 1.5% and 2% methyl alcohol/methylene chloride)to give 2.1 g of the desired product.

후처리

  1. temperatureunder reflux temperature for 8 hours
  2. temperatureThe reaction is cooled
  3. concentrationconcentrated in vacuo
  4. customdried under high vacuum for 1 hour
  5. dissolutionThe crude residue is dissolved in 70 ml of tetrahydrofuran
  6. addition10.0 ml of 1M tetrabutyl ammonium fluoride in tetrahydrofuran is added
  7. additionThe mixture is poured into water
  8. extractionextracted with ethyl acetate
  9. washThe organic layer is washed with saturated sodium chloride
  10. customdried
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0ca647fa90f14fc8ad7c35677835ade3
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387685

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