Water → HCID 20598050, compound

Participants

Reaction Conditions

Reaction Steps

3(S)-(Phenyl-propionyl-amino)-piperidine-1-carboxylic acid tert-butyl ester (168) (100 mg) was dissolved in a mixture of TFA-CH2Cl2 (1 ml, 20%) and stirred for 1 hr. After removal of solvent, the residue was dried under vacuum for 30 min and dissolved in 5 ml of CH2Cl2, washed with sat. K2CO3, dried (Na2SO4), filtered. After evaporation of the solvent, the residue was dissolved in CH3CN (1 ml). Then K2CO3 (125 mg, 3 eq), water (1 ml) and (2-bromoethyl)benzene (0.05 ml, 1.2 eq) was added. The mixture was heated at 70° C. for 12 hr. After cool to room temperature, the mixture was diluted with sat. NaHCO3 (5 ml), extracted with CH2Cl2 (2×10 ml). The combined organic layers were dried (Na2SO4), filtered and evaporated. The residue was purified by silica gel chromatography (100% CH2Cl2, 2%–4% MeOH in CH2Cl2) to give 171 as a colorless oil.

Provenance & Evidence