Bromobenzene → (+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyI-4a-(3-methoxyphenyl)-6-phenyl-6-isoquinolinol

HRID 1739783

反応式

HRID 1739783 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:13]([N:15]1[CH2:24][CH2:23][C@@:22]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)[C@@H:17]([CH2:18][CH2:19][C:20](=[O:33])[CH2:21]2)[CH2:16]1)[CH3:14]>CCCCCC.C1COCC1>[NH4+:15].[OH-:31].[CH2:13]([N:15]1[CH2:24][CH2:23][C@@:22]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)[C@@H:17]([CH2:18][CH2:19][C:20]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)([OH:33])[CH2:21]2)[CH2:16]1)[CH3:14]

参加物

7

反応物 3

HCID 7961BromobenzeneHCID 10517409(+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinoneHCID 178418339Butyllithium

生成物 2

HCID 14923Ammonium HydroxideHCID 86754625(+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyI-4a-(3-methoxyphenyl)-6-phenyl-6-isoquinolinol収率 52.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

30 ml (41.7 mmol) of a 1.4 M solution of n-butyllithium in hexane were added dropwise, under a nitrogen atmosphere and at -55° C., to a solution of 6.5 g (41.7 mmol) of bromobenzene in 30 ml of dry THF. After 1 h the solution was allowed to warm up to -20° C. and a solution of 2.4 g (8.3 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone in 20 ml of dry THF was added. The reaction mixture was allowed to warm up to room temperature overnight, then it was quenched with 30 ml of a 5% HCl solution and the phases were separated. The aqueous phase was extracted with AcOEt, then brought to pH 14 with a 2N NaOH solution and extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 0.79 g of the title compound.

後処理

  1. temperatureto warm up to room temperature overnight
  2. customit was quenched with 30 ml of a 5% HCl solution
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with AcOEt
  5. extractionextracted with AcOEt
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. customThe crude reaction mixture
  9. customwas purified by flash chromatography
  10. washeluting with a mixture CH2Cl2 /MeOH/conc

出典と根拠

ORDレコード
ord-2f8deed0a8bc40f196403bb5701a411d
出典データセット
uspto-grants-1999_10
特許番号
US05968949

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