氢氧化钠 → 1-[(2-Methoxy-3-pyridyl)methyl]-4-(2-phenylphenethyl)piperidine

HRID 1837726笔记

反应方程式

HRID 1837726 反应方程式
[C:1]1([C:7]2[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=2[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][O:22][C:23]1[C:28]([CH:29]=O)=[CH:27][CH:26]=[CH:25][N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O1CCCC1>[CH3:21][O:22][C:23]1[C:28]([CH2:29][N:14]2[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][C:8]3[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:16][CH2:15]2)=[CH:27][CH:26]=[CH:25][N:24]=1

参与物

6

反应物 4

HCID 14798氢氧化钠HCID 5049666三乙酰氧基硼氢化钠HCID 125333912-甲氧基-3-吡啶醛HCID 226783264-(2-Phenylphenethyl)piperidine

产物 1

HCID 226784851-[(2-Methoxy-3-pyridyl)methyl]-4-(2-phenylphenethyl)piperidine收率 80.8%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

181 mg of 4-(2-phenylphenethyl)piperidine synthesized from the corresponding raw material in the same manner as in the above-mentioned process, 150 mg of 2-methoxy-3-pyridinecarboxaldehyde and 226 mg of sodium triacetoxy borohydride were suspended in 5 ml of tetrahydrofuran, and the mixture was stirred for 20 hours at room temperature. The reaction mixture was basified by adding a 1N aqueous sodium hydroxide thereto, and then extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (ethyl acetate:hexane=1:19), to give 213 mg of the title compound as a colorless oil.

后处理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe crude product was purified by NH
  6. customform silica gel column chromatography (ethyl acetate:hexane=1:19)

来源与证据

ORD记录
ord-2fe2379c764742979db2345616087270
来源数据集
uspto-grants-2004_08
专利号
US06784192B2

反应笔记

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