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

HRID 2301083노트

반응식

HRID 2301083 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-48e7c6cece6146d9ad727b3c6084e3cd
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498251B1

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