Imidazole → 2-(5-triisopropylsilanyloxy-1H-indol-3-yl)-ethylamine

HRID 6746

반응식

HRID 6746 반응식
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[NH:6][CH:5]=1.N1C=CN=C1.[CH:19]([Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])([CH3:21])[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[CH:19]([Si:22]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][NH2:1])([CH3:21])[CH3:20]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 5202SerotoninHCID 139400Triisopropylsilyl chloride

생성물 1

HCID 220185062-(5-triisopropylsilanyloxy-1H-indol-3-yl)-ethylamine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-(2-amino-ethyl)-1H-indol-5-ol (3.0 g), imidazole (9.6 g), and triisopropylsilyl chloride (4.5 mL) was stirred in 20 mL N,N-dimethylformamide for 6 h. The solution was diluted with 100 mL of ethyl acetate and washed with 100 mL of sodium carbonate and 100 mL of saturated sodium chloride (3 times). The organic phase was dried over sodium sulfate and the solvent was evaporated. Silica gel chromatography (2% methyl alcohol in dichloromethane) gave 2-(5-triisopropylsilanyloxy-1H-indol-3-yl)-ethylamine (2.6 g). This compound was cyclized with formaldehyde by Procedure OO to afford 6-triisopropylsilanyloxy-2,3,4,9-tetrahydro-1H-β-carboline, which was protected with tert-butoxycarbonyl group by Procedure CC to give 6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester.

후처리

  1. washwashed with 100 mL of sodium carbonate and 100 mL of saturated sodium chloride (3 times)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-5a7e3236c03546a79481668dbf1dafbb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

연결된 노트

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