Dichloromethane → rac-(1R,3S)-3-(aminomethyl)cyclopentane-1-carboxylic acid

HRID 2187994ノート

反応式

HRID 2187994 の反応式
[N:1]([CH2:4][C@@H:5]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6]1)=[N+]=[N-].ClCCl>CO.CN(C)C=O.[Pd]>[NH2:1][CH2:4][C@@H:5]1[CH2:9][CH2:8][C@H:7]([C:10]([OH:12])=[O:11])[CH2:6]1

参加物

6

反応物 2

HCID 6344DichloromethaneHCID 86758275cis-3-Azidomethylcyclopentancarboxylic acid

生成物 1

HCID 42614337rac-(1R,3S)-3-(aminomethyl)cyclopentane-1-carboxylic acid

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of cis-3-azidomethylcyclopentancarboxylic acid (0.9 g, 5.3 mmol) in methanol (about 30 mL) was hydrogenated at about 50 psi and room temperature in the presence of 10% Pd on carbon (about 40 mg) for about 1 h. The catalyst was removed by filtration and the filtrate concentrated to give a syrup. When the syrup was dissolved in dimethylformamide and dichloromethane for acetylation (next step), formation of some white precipitate occurred. The precipitate was collected by filtration, washed with dichloromethane and dried to give cis-3-aminomethylcyclopentanecarboxylic acid as a white powder, mp 186-188° C. The yield of syrup was 0.7 g (100%). The white solid obtained was about 0.35 g. The remainder of the material from the dimethylformamide and dichloromethane mixture was not recovered, but was used for the acetylation step.

後処理

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated
  3. customto give a syrup
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with dichloromethane
  6. customdried

出典と根拠

ORDレコード
ord-ea36b694c0284745a1c407d438a60372
出典データセット
uspto-grants-2002_06
特許番号
US06410594B1

反応ノート

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