N-Acetyl-D-leucine → (1R)-5-(1,1-Dimethylethyl)-2,3-dihydro-1H-inden-1-amine

HRID 451599

Reaktionsgleichung

Reaktionsgleichung von HRID 451599
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH2:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].C(N[C@@H](C(O)=O)CC(C)C)(=O)C>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([NH2:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 1241420N-Acetyl-D-leucineHCID 115066015-tert-butyl-2,3-dihydro-1H-inden-1-amine

Produkt 1

HCID 24777767(1R)-5-(1,1-Dimethylethyl)-2,3-dihydro-1H-inden-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

5-tert-Butyl-2,3-dihydro-1H-inden-1-ylamine (11.70 g, 44.4% ee), N-acetyl-(D)-leucine (11.78 g), and methanol (120 mL) were combined and heated at 65° C. for 1 hour. The solution was allowed to cool to ambient temperature. The solids were filtered and washed with toluene. The solid was then resuspended in methanol (125 mL) and brought to reflux. The solution was allowed to cool to ambient temperature and the solids were filtered. The solid was dried at 40° C. under reduced pressure to provide the title compound (98.7% ee).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationThe solids were filtered
  3. washwashed with toluene
  4. temperatureto reflux
  5. temperatureto cool to ambient temperature
  6. filtrationthe solids were filtered
  7. customThe solid was dried at 40° C. under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-141fbe474aec400ca21ec3bfda1ced7a
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487116B2

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