Reaktion #2004

Reaktionsgleichung

benzyl ester

(R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester

→

product

Ausbeute 102.1%

(R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid

Ausbeute 102.1%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was degassed
2. 2
   workup.ADDITIONa hydrogen atmosphere introduced over the reactants
3. 3
   Sonstigefor 32 hours
4. 4
   SonstigeThe reaction products were isolated
5. 5
   Filtrationby filtering the reaction mixture through a Celite plug
6. 6
   WaschenThe plug was washed with additional ethyl acetate (3×10 mL)
7. 7
   SonstigeThe combined filtrates were evaporated under vacuum

Vorschrift

The benzyl ester (0.82 g, 1.71 mmol) obtained in Step C and 10% palladium on carbon (150 mg) were stirred together in ethyl acetate (5 mL). The solution was degassed and a hydrogen atmosphere introduced over the reactants using a balloon for 32 hours. The reaction products were isolated by filtering the reaction mixture through a Celite plug. The plug was washed with additional ethyl acetate (3×10 mL). The combined filtrates were evaporated under vacuum to afford the product (680 mg, 102%). 1H NMR (400 MHz, CDCl3): 1.30 (s, 9H), 1.41 (s, 6H), 3.32 (dd, 1H), 3.42 (m, 1H), 4.87 (br s, 1H), 6.82 (d, 1H), 7.13-7.35 (m, 8H), 7.60 (d, 1H), 8.28 (br s, 1H).

Quelle