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

HRID 1373089Notes

Reaction equation

HRID 1373089 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-15 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f4744204b74e40a99fc88641fa6937d5
Source dataset
uspto-grants-2007_01
Patent number
US07160900B2

Reaction notes

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