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

HRID 2187994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187994
[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

Komponenten

6

Edukt 2

HCID 6344DichloromethaneHCID 86758275cis-3-Azidomethylcyclopentancarboxylic acid

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ea36b694c0284745a1c407d438a60372
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410594B1

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