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

HRID 1469228

反応式

HRID 1469228 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5294d322e3a41acb139a391b41bed2f
出典データセット
uspto-grants-2015_04
特許番号
US09006264B2

関連ノート

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