Water → rac-tert-butyl N-((1R,2R)-2-aminocyclopentyl)carbamate

HRID 902838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 902838
[C@@H:1]1([NH2:7])[CH2:5][CH2:4][CH2:3][C@H:2]1[NH2:6].[C:8]([O:12][C:13](ON=C(C1C=CC=CC=1)C#N)=[O:14])([CH3:11])([CH3:10])[CH3:9].O>C(Cl)Cl.C(N(CC)CC)C>[NH2:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@H:1]1[NH:7][C:13](=[O:14])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9]

Komponenten

6

Edukt 3

HCID 962WaterHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile2×HCID 243938Cyclopentane-1,2-diamine

Produkt 1

HCID 17040217rac-tert-butyl N-((1R,2R)-2-aminocyclopentyl)carbamateAusbeute 98,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(±)-trans-1,2-Cyclopentanediamine (WO98/30574) (692 mg) was dissolved in methylene chloride (10 ml), to which triethylamine (1.1 ml) and 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) were added, and the mixture was stirred at 0° C. for 1 hour. Thereafter, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (493 mg) were additionally added, and the mixture was stirred at room temperature for 7 hours. Water was added to the reaction mixture to separate an organic layer. The organic layer was washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The residue was purified by flash column chromatography on silica gel (methylene chloride:methanol=9:1) to obtain the title compound (395 mg).

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was stirred at room temperature for 7 hours
  3. customto separate an organic layer
  4. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by flash column chromatography on silica gel (methylene chloride:methanol=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-403b4eab9f8d4282ab674bc3db83d850
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365205B2

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