Trifluoroacetic acid → HCID 59166435, compound

HRID 1484241Notes

Reaction equation

HRID 1484241 reaction equation
[OH:1][C:2]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[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([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:3][CH2:4][N:5]([C@H:8]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:9]([OH:11])=[O:10])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59166502(S)-1-Phenylethyl(R)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-2-phenylacetate

Product 1

HCID 59166435HCID 59166435, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-phenylethyl (R)-2-(4-hydroxy-4-phenylpiperidin-1-yl)-2-phenylacetate (0.350 g, 0.84 mmol) in dichloromethane (5 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 white solid (0.230 g, 88%). LCMS: Anal. Calcd. for C19H21NO3: 311. found: 312 (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-87be4843bf214c63abc549e5681c236c
Source dataset
uspto-grants-2016_08
Patent number
US09421192B2

Reaction notes

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