Methanol → Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate

HRID 382809ノート

反応式

HRID 382809 の反応式
[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]2[CH2:12][N:13]([CH3:22])[CH2:14][CH2:15]/[C:16]/2=[CH:17]\[C:18]([O:20][CH3:21])=[O:19])=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2].[H][H].[CH3:27][OH:28]>[Pd]>[C:18]([O:20][CH2:21][CH3:27])(=[O:19])[CH3:17].[CH3:8][OH:9].[NH4+:13].[OH-:28].[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C@H:11]2[C@@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]([CH3:22])[CH2:12]2)=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2].[CH2:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C@H:11]2[C@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]([CH3:22])[CH2:12]2)=[CH:5][C:4]=1[O:23][CH3:24])[CH3:2]

参加物

7

反応物 3

HCID 887MethanolHCID 86757543methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetateHCID 178418361HCID 178418361、化合物

生成物 3

HCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 69823052Methyl trans-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate収率 21%HCID 69823475Methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate収率 77%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

g 2) A solution of 11.7 g (35.3 mmol) of methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate in 100 ml of methanol was treated with 500 mg of Pd on charcoal and hydrogenated with hydrogen at room temperature for 12 hours. The catalyst was filtered off and the filtrate was evaporated. Chromatography (silica gel, ethyl acetate/methanol/NH4OH 200:10:1) yielded 9.14 g (77%) of methyl cis-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.23 (silica gel ethyl acetate methanol/NH4OH 200:10:1) and 2.56 g (21%) of methyl trans-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-yl]-acetate as a colorless oil, Rf=0.12 (silica gel, ethyl acetate/methanol/NH4OH 200:10:1).

後処理

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

出典と根拠

ORDレコード
ord-10d2d1a2c6cc448f879dc2afd98ac5e9
出典データセット
uspto-grants-2001_10
特許番号
US06310208B1

反応ノート

読み込み中…