Sodium Bicarbonate → 1-{1-[2-(4-hydroxy-7-methoxy-2,2-dimethylchroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide

HRID 494965ノート

反応式

HRID 494965 の反応式
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:35])([CH3:34])[O:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO>[OH:36][CH:7]1[C:6]2[C:11](=[C:12]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([C:30]([NH:32][CH3:33])=[O:31])[CH:28]=5)[CH:23]=[CH:22]4)[CH2:17][CH2:16]3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:10][C:9]([CH3:35])([CH3:34])[CH2:8]1

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 11677552E-2110 free base

生成物 1

HCID 576828731-{1-[2-(4-hydroxy-7-methoxy-2,2-dimethylchroman-8-yl)ethyl]piperidin-4-yl}-N-methyl-1H-indole-6-carboxamide収率 83.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

259 mg of 1-(1-(2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl)piperidin-4-yl)-N-methyl-1H-indole-6-carboxamide was dissolved in 5 ml of methanol. Thereafter, 60 mg of sodium borohydride was added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature overnight. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate) and then purified by silica gel column chromatography (ethyl acetate-methanol), so as to obtain 216 mg of the subject compound.

後処理

  1. temperaturewhile cooling on ice
  2. extractionfollowed by extraction with methylene chloride
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate)
  6. custompurified by silica gel column chromatography (ethyl acetate-methanol)

出典と根拠

ORDレコード
ord-e055be2c2f3045ff914c75cede837b3e
出典データセット
uspto-grants-2009_05
特許番号
US07538123B2

反応ノート

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