Methanol → (R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide

HRID 1351935ノート

反応式

HRID 1351935 の反応式
C1C2C(COC(=O)[NH:17][C@H:18]([CH3:37])[C:19]([C:21]3[C:29]4[C:24](=[C:25]([C:30](=[O:36])[N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)=O)C3C(=CC=CC=3)C=2C=CC=1.[BH4-].[Na+].CO>C(#N)C.CC(O)C>[CH2:34]([N:31]([CH2:32][CH3:33])[C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[NH:23][CH:22]=[C:21]2[CH2:19][C@H:18]([NH2:17])[CH3:37])=[O:36])[CH3:35]

参加物

6

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 69458837(R)-[2-(7-diethylcarbamoyl-1H-indol-3-yl)-1-methyl-2-oxoethyl]carbamic acid 9H-fluoren-9-ylmethyl ester

生成物 1

HCID 69457261(R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide収率 66%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6342Acetonitrile溶媒

実験手順

A solution of (R)-[2-(7-diethylcarbamoyl-1H-indol-3-yl)-1-methyl-2-oxoethyl]carbamic acid 9H-fluoren-9-ylmethyl ester (10.24 g, 20.1 mmol) in a mixture of acetonitrile (134 mL) and 2-propanol (7.7 ml) is added sodium borohydride (3.80 g, 100 mmol) in portions at room temperature with stirring, and the mixture is refluxed for 4 hours. The reaction solution is cooled to room temperature, and thereto is added dropwise methanol (200 ml). The reaction mixture is concentrated to dryness under reduced pressure. To the residue are added ethyl acetate and water, and the mixture is stirred. The organic layer is separated, washed with a saturated brine, and dried over anhydrous sodium sulfate. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (methanol/(a saturated ammonia solution in chloroform)=1/100) to give the desired (R)-3-(2-aminopropyl)-1H-indole-7-carboxylic acid diethylamide (3.60 g, yield: 66%).

後処理

  1. temperaturethe mixture is refluxed for 4 hours
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. additionTo the residue are added ethyl acetate and water
  4. stirringthe mixture is stirred
  5. customThe organic layer is separated
  6. washwashed with a saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent is evaporated under reduced pressure
  9. customthe residue is purified by silica gel column chromatography (methanol/(a saturated ammonia solution in chloroform)=1/100)

出典と根拠

ORDレコード
ord-156e996847124439a0efd29a1fa155b3
出典データセット
uspto-grants-2007_05
特許番号
US07217724B2

反応ノート

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