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

HRID 68263Notes

Reaction equation

HRID 68263 reaction equation
[OH:1][C:2]1([CH3:26])[CH2:7][CH2:6][N:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]([O:11][C@H](C2C=CC=CC=2)C)=[O:10])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>ClCCl>[OH:1][C:2]1([CH3:26])[CH2:3][CH2:4][N:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]([OH:11])=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59166531(S)-1-Phenylethyl(R)-2-(4-hydroxy-4-methylpiperidin-1-yl)-2-phenylacetate

Product 1

HCID 59166390(R)-2-(4-Hydroxy-4-methylpiperidin-1-yl)-2-phenylacetic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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)+.

Workup

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

Sources & evidence

ORD record
ord-cc644776760f4236942d011fd66c822d
Source dataset
uspto-grants-2014_09
Patent number
US08822444B2

Reaction notes

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