Dimethylformamide → cis-8-fluoro-2-propyl-1,3,4,4a, 5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

HRID 382814ノート

反応式

HRID 382814 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:14]3[C@H:9]([CH2:10][CH2:11][NH:12][CH2:13]3)[CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1.Br[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:14]3[C@H:9]([CH2:10][CH2:11][N:12]([CH2:18][CH2:19][CH3:20])[CH2:13]3)[CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 86757545cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

生成物 1

HCID 86757546cis-8-fluoro-2-propyl-1,3,4,4a, 5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one収率 63.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
125 °C

実験手順

A mixture of 0.29 g (1.32 mmol) of cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one, 0.12 ml (1.39 mmol) of bromopropane, 0.2 g (1.45 mmol) of potassium carbonate and 20 ml of anhydrous DMF was heated to 125° C. for 1 hour. Subsequently, the mixture was poured into 3 ml of water and extracted once with 50 ml of ethyl acetate. The organic phase was washed once with 40 ml of saturated sodium chloride solution, dried (MgSO4) and concentrated in a vacuum. The crude product obtained was purified by column chromatography on silica gel (methylene chloride/methanol/NH4OH 9:1:0.2). There were obtained 220 mg (63%) of cis-8-fluoro-2-propyl-1,3,4,4a, 5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one as a yellow oil, which was converted with MeOH/HCl into the hydrochloride with m.p. >220°.

後処理

  1. extractionextracted once with 50 ml of ethyl acetate
  2. washThe organic phase was washed once with 40 ml of saturated sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in a vacuum
  5. customThe crude product obtained
  6. customwas purified by column chromatography on silica gel (methylene chloride/methanol/NH4OH 9:1:0.2)

出典と根拠

ORDレコード
ord-fe96d375b20c48fd8326b4dac1cd99aa
出典データセット
uspto-grants-2001_10
特許番号
US06310208B1

反応ノート

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