Hydrochloric Acid → HCID 18653158, compound

Participants

Reaction Steps

CBZ-L-Valine (12.6 g, 0.05 mol) and triethylamine (5.06 g 0.05 mol) were dissolved in THF (100 mL) and then cooled to 0°-5° C, with an ice water bath. Ethyl chloroformate (5.44 g, 0.05 mol) in THF (35 mL) was added dropwise at 0°-5° C. Following the addition the mixture was stirred for one hour in the cold. Ethyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride (14.5 g, 0.06 mol) and triethylamine (6.1 g, 0.06 mol) in CH2Cl2 (60 mL) and THF (30 mL) were added at 0° C. The reaction mixture as allowed to sit at room temperature overnight. Evaporation of the solvent yielded a viscous semisolid which was treated with ethyl acetate followed by 1N HCl and the layers were separated. The organic extract was washed with 1N aqueous HCl followed by 5% aqueous Na2CO3 and saturated aqueous NaCl-solution. After drying over MgSO4 , filtration and evaporation under reduced pressure afforded an oil (12.5 g) which was purified over silica gel using hexane: ethyl acetate (8:2) as eluent. Collected 2.9 g of the desired product as a viscous oil.

Provenance & Evidence