1-tert-Butyl 6-methyl 1H-indole-1,6-dicarboxylate → tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 1774208노트

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HRID 1774208 반응식
[H-].C([Al+]CC(C)C)C(C)C.[N:11]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](OC)=[O:21])[CH:18]=2)[CH:13]=[CH:12]1>C1(C)C=CC=CC=1>[OH:21][CH2:20][C:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][N:11]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:15][CH:16]=1

참가 물질

4

반응물 2

HCID 208216591-tert-Butyl 6-methyl 1H-indole-1,6-dicarboxylateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate수율 65.9%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-50 °C

실험 절차

Diisobutylaluminum hydride (1M in toluene, 12 mL, 12 mmol) was added to a solution of 1-tert-butyl 6-methyl 1H-indole-1,6-dicarboxylate (1.38 g, 5.00 mmol) in toluene (15 mL) at −50° C. over 10 minutes. After being stirred at −50° C. for 30 minutes, the reaction was quenched with methanol (2.5 mL) and water (2.5 mL). The resulting precipitate was filtered off, and the filtrate was evaporated. The residue was purified by silica gel chromatography, eluting with petroleum ether/ethyl acetate (5:1 to 1:1) to afford tert-butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate (815 mg, 55% yield) as an oil. LCMS (ESI) m/z 174.3 [M+H-18-56]+, 230.3 [M+H-18]+.

후처리

  1. customthe reaction was quenched with methanol (2.5 mL) and water (2.5 mL)
  2. filtrationThe resulting precipitate was filtered off
  3. customthe filtrate was evaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with petroleum ether/ethyl acetate (5:1 to 1:1)

출처 및 근거

ORD 기록
ord-b0d148de6211498683d1556c70858187
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09259470B2

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