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

HRID 382809노트

반응식

HRID 382809 반응식
[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]

참가 물질

7

반응물 3

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

생성물 3

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

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-10d2d1a2c6cc448f879dc2afd98ac5e9
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310208B1

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