Chloroacetonitrile → 2-(2,3,3a,8b-Tetrahydrocyclopenta[b]Indol-4(1H)-yl)Acetonitrile

HRID 723320ノート

反応式

HRID 723320 の反応式
[CH2:1]1[CH:12]2[CH:4]([NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:16][C:17]#[N:18]>CS(C)=O>[CH2:1]1[CH:12]2[CH:4]([N:5]([CH2:16][C:17]#[N:18])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 7856Chloroacetonitrile2 回HCID 24758Sodium hydride2 回HCID 218735741,2,3,3a,4,8b-Hexahydrocyclopenta[b]indole

生成物 1

HCID 218735712-(2,3,3a,8b-Tetrahydrocyclopenta[b]Indol-4(1H)-yl)Acetonitrile

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a stirred solution of 1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole (22 mmol, 3.5 g) in DMSO (44 mL) was added 60% sodium hydride (24 mmol, 0.97 g) portionwise, followed by 2-chloroacetonitrile (33 mmol, 2.1 mL). The reaction mixture stirred at ambient temperature for 18 h and then additional 60% sodium hydride (22 mmol, 0.88 g) and 2-chloroacetonitrile (24 mmol, 1.5 mL) was added. The reaction was heated to 60° C. for 18 h. The reaction was concentrated and the diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash column chromatography through silica gel (elution with 60% ethyl acetate-hexanes) to afford the desired material.

後処理

  1. temperatureThe reaction was heated to 60° C. for 18 h
  2. concentrationThe reaction was concentrated
  3. additionthe diluted with ethyl acetate and water
  4. customThe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash column chromatography through silica gel (elution with 60% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-42ff2f2fa64c4c63948ed932dc92cfba
出典データセット
uspto-grants-2006_11
特許番号
US07141563B2

反応ノート

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