Réaction #155445

ord-cc644776760f4236942d011fd66c822d

Équation de réaction

C[C@H](OC(=O)[C@@H](c1ccccc1)N1CCC(C)(O)CC1)c1ccccc1
(S)-1-phenylethyl(R)-2-(4-hydroxy-4-methylpiperidin-1-yl)-2-phenylacetate
O=C(O)C(F)(F)F
trifluoroacetic acid
CC1(O)CCN([C@@H](C(=O)O)c2ccccc2)CC1
title compound
Rendement 98.7%
CC1(O)CCN([C@@H](C(=O)O)c2ccccc2)CC1
(R)-2-(4-Hydroxy-4-methylpiperidin-1-yl)-2-phenylacetic acid
Rendement 98.7%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08822444B2uspto-grants-2014_09