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1-Phenethylamine → (+)-Ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate

HRID 345576
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인쇄 미리보기

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HRID 345576 반응식
Cl.ClCC1C=CC(N2C=CN=C2)=CC=1.[CH3:15][O:16][CH:17]1[C:22](=O)[CH2:21][CH2:20][N:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:18]1.[CH3:29][CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH2:31].S1C=CC=C1.[H][H]>C(O)C.[Pd].CO>[CH3:15][O:16][C@H:17]1[C@@H:22]([NH:31][CH:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:29])[CH2:21][CH2:20][N:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:18]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 74081-PhenethylamineHCID 8030ThiopheneHCID 2724451Ethyl 3-methoxy-4-oxopiperidine-1-carboxylateHCID 197946621-[4-(chloromethyl)phenyl]-1H-imidazole hydrochlorideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67914576(+)-Ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate
수율 51%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 887Methanol용매

실험 절차

A solution of 20 parts of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate, 12 parts of (-)-α-methylbenzenemethanamine, 2 parts of a solution of thiophene in ethanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 4 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was purified by HPLC using a mixture of hexane, trichloromethane and methanol (50:49.5:0.5 by volume) as eluent. The pure A-fractions were collected and the eluent was evaporated, yielding 15.62 parts (51%) of (-)-ethyl cis-3-methoxy-4-[(1-phenylethyl)amino]-1-piperidinecarboxylate as a residue (intermediate 103).

후처리

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by HPLC
  4. additiona mixture of hexane, trichloromethane and methanol (50:49.5:0.5 by volume) as eluent
  5. customThe pure A-fractions were collected
  6. customthe eluent was evaporated

출처 및 근거

ORD 기록
ord-57194a63cb7d4511a02e1f1861792cf9
출처 데이터셋
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05057525

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