Ammonium Chloride → 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxypiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

HRID 23548ノート

反応式

HRID 23548 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:30])=[CH:16][C:17]([N:18]3[CH2:23][CH2:22][C:21](=[O:24])[CH:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:19]3)=[C:12]2[C:11]([CH3:31])=[C:10]1[CH3:32].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:30])=[CH:16][C:17]([N:18]3[CH2:23][CH2:22][CH:21]([OH:24])[CH:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:19]3)=[C:12]2[C:11]([CH3:31])=[C:10]1[CH3:32]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 121346571-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 121346591-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxypiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine収率 26.8%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
-15 °C

実験手順

In ethanol (3.0 mL) was dissolved 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (0.13 g), and the solution was cooled to −15° C. Then, sodium boro hydride (26 mg) was added thereto and the resulting mixture was stirred overnight while being slowly heated to 0° C. A saturated aqueous ammonium chloride solution was poured into the reaction mixture, which was then extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=50:1) to obtain 1-(2,4-dichlorophenyl)-4-(3-ethoxycarbonyl-4-hydroxy-piperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (35 mg).

後処理

  1. temperaturewhile being slowly heated to 0° C
  2. extractionwas then extracted three times with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: chloroform-methanol=50:1)

出典と根拠

ORDレコード
ord-344f694e4e8b43a8b79d20ca972e5a1c
出典データセット
uspto-grants-2005_02
特許番号
US06852732B2

反応ノート

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