Sodium triacetoxyborohydride → N-(3,4-dichlorophenyl)-4-[((3R)-1-{[6-(2-methoxyethoxy)pyridin-3-yl]methyl}piperidin-3-yl)methyl]piperazine-1-carboxamide

HRID 603215ノート

反応式

HRID 603215 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:25][O:26][CH2:27][CH2:28][O:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][N:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]3[CH2:24][CH2:23][CH2:22][N:21]([CH2:34][C:33]4[CH:32]=[N:31][C:30]([O:29][CH2:28][CH2:27][O:26][CH3:25])=[CH:37][CH:36]=4)[CH2:20]3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 150670976-(2-Methoxyethoxy)nicotinaldehydeHCID 57656731N-(3,4-Dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide

生成物 1

HCID 57656756N-(3,4-dichlorophenyl)-4-[((3R)-1-{[6-(2-methoxyethoxy)pyridin-3-yl]methyl}piperidin-3-yl)methyl]piperazine-1-carboxamide収率 27%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of the hydrochloride salt of N-(3,4-dichlorophenyl)-4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxamide (442 mg, 1.00 mmol) in dichloromethane (40 ml) was added 6-(2-methoxyethoxy)nicotinaldehyde (199 mg, 1.00 mmol) and the cloudy mixture stirred at room temperature for 10 minutes. Polymer supported sodium triacetoxyborohydride (555 mg, 1.50 mmol) was added and the reaction stirred at room temperature overnight. The mixture was filtered, the filtrate washed with water (20 ml), organic extract dried (Na2SO4), filtered and evaporated to an oil. Flash column chromatography (10 gram Isolute silica column eluting; CH2Cl2 to 10% MeOH/CH2Cl2) yielded N-(3,4-dichlorophenyl)-4-[((3R)-1-{[6-(2-methoxyethoxy)pyridin-3-yl]methyl}piperidin-3-yl)methyl]piperazine-1-carboxamide (145 mg, 27%) as a white foam.

後処理

  1. additionwas added
  2. stirringthe reaction stirred at room temperature overnight
  3. filtrationThe mixture was filtered
  4. washthe filtrate washed with water (20 ml)
  5. extractionorganic extract
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to an oil
  9. washFlash column chromatography (10 gram Isolute silica column eluting; CH2Cl2 to 10% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-2a4a268b70db4133be688487824544b1
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

反応ノート

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