반응 #62806

반응 방정식

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

용매

CHCl3

반응 조건

후처리

1. 1
   workup.ADDITIONwas added at -5° C
2. 2
   여과The reaction mixture was filtered
3. 3
   농축the filtrate was concentrated to dryness
4. 4
   기타to give a semi-solid, which
5. 5
   기타was purified
6. 6
   세척eluting with ethyl acetate:hexane (1:1)

실험 절차

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°.

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