1-Phenethylamine, (+)- → (R)-1-phenylethanaminium (1S,3aR,6aS)-2(t-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

HRID 473542

Reaktionsgleichung

Reaktionsgleichung von HRID 473542
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@@H:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C@H:9]1[C:16]([O-:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:21]1([C@H:20]([NH3+:27])[CH3:19])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 6431891-Phenethylamine, (+)-HCID 532496462-(Tert-butoxycarbonyl)octahydrocyclopenta[C]pyrrole-1-carboxylic acid

Produkt 1

HCID 87377471(R)-1-phenylethanaminium (1S,3aR,6aS)-2(t-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylateAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
23.5 °C

Versuchsvorschrift

To a solution of racemic N-t-butyloxycarbonyl-3-azabicyclo[3.3.0]octane-2-carboxylic acid (4.66 g) in ethyl acetate (100 mL) was added (R)-α-methylbenzylamine (56.7 g) and the solution was stirred for 16 hr at 22-25° C. The mixture was filtered and the solids were rinsed with ethyl acetate. The solids were dried at 20-30° C. under vacuum for 4 hours to give 1.47 g of product (43%, 82% ee, 92:8 ratio of exo:endo diastereomers).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe solids were rinsed with ethyl acetate
  3. customThe solids were dried at 20-30° C. under vacuum for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-1371e2e08d114a3f954ef3811887320b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637457B2

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