Sodium hydride → 2-Tert-butoxycarbonyl-9-methoxycarbonylmethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole

HRID 2301083ノート

反応式

HRID 2301083 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

生成物 1

HCID 110784542-Tert-butoxycarbonyl-9-methoxycarbonylmethyl-1,2,3,4-tetrahydropyrido[3,4-b]indole収率 77%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 218 mg (5.45 mmol) portion of sodium hydride was added to 12 ml of DMF solution containing 0.99 g (3.64 mmol) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole, and the mixture was stirred at room temperature for 30 minutes, mixed with 0.52 ml (5.45 mmol) of methyl bromoacetate and again stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the thus obtained oily material was purified by a silica gel column chromatography (200 cc; elution by ethyl acetate-hexane=1:3) to obtain 0.96 g of the title compound (77% in yield).

後処理

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialAfter drying (Na2SO4)
  4. customthe solvent was removed by evaporation under a reduced pressure
  5. customthe thus obtained oily material was purified by a silica gel column chromatography (200 cc; elution by ethyl acetate-hexane=1:3)

出典と根拠

ORDレコード
ord-48e7c6cece6146d9ad727b3c6084e3cd
出典データセット
uspto-grants-2002_12
特許番号
US06498251B1

反応ノート

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