Water → 3-Hydroxymethyl-beta-carboline

HRID 574129

반응식

HRID 574129 반응식
[C:1]([C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3)(OC)=[O:2].[BH4-].[Na+].O>C1COCC1>[OH:2][CH2:1][C:5]1[N:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][CH:13]=[CH:12][CH:11]=3

참가 물질

5

반응물 3

HCID 962WaterHCID 107704Methyl 9H-pyrido(3,4-b)indole-3-carboxylateHCID 4311764Sodium borohydride

생성물 1

HCID 53533383-Hydroxymethyl-beta-carboline수율 84.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3.5 grams (15 mmol) of 3-carbomethoxy-β-carboline were suspended in 300 ml THF, 2.7 grams (75 mmol) sodium borohydride were added and the mixture was stirred at room temperature for 12 hours. The mixture was then cooled, 50 ml water was added and the resulting mixture was stirred overnight. The solvent was evaporated under reduced pressure and water (300 ml) was again added. The aqueous suspension was extracted with dichloromethane, followed by ethylacetate, the organic extracts were combined, and the solvent was evaporated under reduced pressure. The remaining residue was purified by column chromatography on silica gel, using and a 9:1 mixture of ethylacetate and methanol as eluent, to give 3-(hydroxymethyl)-β-carboline (2.5 grams, 81% yield).

후처리

  1. temperatureThe mixture was then cooled
  2. stirringthe resulting mixture was stirred overnight
  3. customThe solvent was evaporated under reduced pressure and water (300 ml)
  4. additionwas again added
  5. extractionThe aqueous suspension was extracted with dichloromethane
  6. customthe solvent was evaporated under reduced pressure
  7. customThe remaining residue was purified by column chromatography on silica gel
  8. additiona 9:1 mixture of ethylacetate and methanol as eluent

출처 및 근거

ORD 기록
ord-c666e84aa64b4cfc94e963aa8033cbac
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034872B2

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