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

HRID 1078790ノート

反応式

HRID 1078790 の反応式
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(CC)C(C)C)(C)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

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 152855547-[[(1,1-Dimethylethyl)dimethylsily]oxy]-1,2,3,4-tetrahydro-6-methoxyisoquinolineHCID 19042070alpha-(5-Bromopentyl)-alpha-(cyclohexylthio)-3,4-dimethoxybenzeneacetonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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-diisopropyl 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.

後処理

  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

出典と根拠

ORDレコード
ord-155dd66a84b64974a607c71bb43624ef
出典データセット
uspto-grants-1996_08
特許番号
US05550149

反応ノート

読み込み中…