Reaction #155445

Reaction equation

(S)-1-phenylethyl(R)-2-(4-hydroxy-4-methylpiperidin-1-yl)-2-phenylacetate

trifluoroacetic acid

→

title compound

Yield 98.7%

(R)-2-(4-Hydroxy-4-methylpiperidin-1-yl)-2-phenylacetic acid

Yield 98.7%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe volatiles were subsequently removed in vacuo
2. 2
   Otherthe residue was purified by reverse-phase preparative HPLC (Primesphere C-18, 20×100 mm

Procedure

To a solution of (S)-1-phenylethyl(R)-2-(4-hydroxy-4-methylpiperidin-1-yl)-2-phenylacetate (0.185 g, 0.52 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL) and the mixture was stirred at room temperature for 2 hours. The volatiles were subsequently removed in vacuo and the residue was purified by reverse-phase preparative HPLC (Primesphere C-18, 20×100 mm; CH3CN—H2O-0.1% TFA) to give the title compound (as TFA salt) as a pale bluish solid (0.128 g, 98%). LCMS: Anal. Calcd. for C14H19NO3: 249. found: 250 (M+H)+.

Source