Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate → Ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

HRID 1363522

반응식

HRID 1363522 반응식
[OH:1][C:2]1([CH2:13][N+:14]([O-])=O)[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:14][CH2:13][C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1

참가 물질

4

반응물 1

HCID 22708806Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate

생성물 1

HCID 14049029Ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

A mixture of ethyl 4-hydroxy-4-(nitromethyl)piperidine-1-carboxylate (5.2 g, 22.4 mmol) and 20% palladium hydroxide on carbon (0.50 g) in ethanol (190 mL) was hydrogenated at 35 psi (2.4×105 Pa) on a Parr apparatus for 5 h. The mixture was filtered through CELITE filter agent and the filtrate was concentrated. By 1H NMR analysis, the reaction was incomplete and the crude material was subjected to the reaction conditions again with fresh 20% palladium hydroxide on carbon (0.50 g) for another 24 h. The mixture was filtered through CELITE filter agent and the filtrate was concentrated to provide ethyl 4-(aminomethyl)-4-hydroxypiperidine-1-carboxylate, which was concentrated from chloroform to remove residual ethanol before using in the next reaction.

후처리

  1. filtrationThe mixture was filtered through CELITE
  2. filtrationfilter agent
  3. concentrationthe filtrate was concentrated
  4. customthe crude material was subjected to the reaction conditions again with fresh 20% palladium hydroxide on carbon (0.50 g) for another 24 h
  5. filtrationThe mixture was filtered through CELITE
  6. filtrationfilter agent
  7. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-1387acf13928454e99b12c92bfa81453
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884207B2

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