Reaktion #62806

Reaktionsgleichung

benzyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate tosylate

N-methylmorpholine

dicyclohexylcarbodiimide

pyruvic acid

→

benzyl N-pyruvoyl-(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at -5° C
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Einengenthe filtrate was concentrated to dryness
4. 4
   Sonstigeto give a semi-solid, which
5. 5
   Sonstigewas purified
6. 6
   Wascheneluting with ethyl acetate:hexane (1:1)

Vorschrift

13.17 g of benzyl (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate tosylate (N. Yoneda, et al., Chem.Pharm.Bull., 31, 312 (1983)) was suspended in 30 mL CHCl3. N-methylmorpholine was added until the pH was 7, 6.8 g of dicyclohexylcarbodiimide and 3.17 g of pyruvic acid was added at -5° C. The reaction mixture was stirred at -50° C. for one hour and 0° C. for 48 hours. The reaction mixture was filtered, and the filtrate was concentrated to dryness to give a semi-solid, which was purified by passing through a silica gel column and eluting with ethyl acetate:hexane (1:1) to give benzyl N-pyruvoyl-(S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate as a yellow oil, [α]D25 -10.3°.

Quelle