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

HRID 2226931ノート

反応式

HRID 2226931 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec0f9592505e45bdb33ea398a1dd417e
出典データセット
uspto-grants-1994_09
特許番号
US05350762

反応ノート

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