Aluminium lithium hydride → 1,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanol

HRID 2226931노트

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HRID 2226931 반응식
C([O:3][C:4]([CH:6]1[CH2:26][C:9]2[N:10]([CH3:25])[C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:15][C:16]=3[C:8]=2[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:19]1([CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]3[N:10]([CH3:25])[C:9]4[CH2:26][CH:6]([CH2:4][OH:3])[CH2:7][C:8]=4[C:16]=3[CH:15]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 542643981,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-carboxylic acid ethyl ester

생성물 1

HCID 189639931,2,3,4-Tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-methanol수율 70.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

To a solution of 1,2,3,4-tetrahydro-7-phenylmethoxy-4-methycyclopent[b]indole-2-carboxylic acid ethyl ester (2.0 g, 0.006 mole) in 50 ml of dry tetrahydrofuran, was added lithium aluminum hydride (1M solution in tetrahydrofuran, 10 ml, 0.01 mole). After stirring at 70° C. for one hour, the mixture was cooled, quenched with 2 ml of saturated ammonium chloride solution, filtered, and the filtrate concentrated to a brown oil, ~2 g. This oil was eluted on a silica gel column with 10% methanol/dichloromethane via HPLC. The desired fractions were combined and concentrated to a tan oil, which solidified on standing to give 1.3 g of the product, m.p. 83°-85° C.

후처리

  1. temperaturethe mixture was cooled
  2. customquenched with 2 ml of saturated ammonium chloride solution
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated to a brown oil, ~2 g
  5. washThis oil was eluted on a silica gel column with 10% methanol/dichloromethane via HPLC
  6. concentrationconcentrated to a tan oil, which

출처 및 근거

ORD 기록
ord-ec0f9592505e45bdb33ea398a1dd417e
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05350762

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