Trifluoroacetic acid → 3,3-Difluoro-4-(4-methoxyphenyl)piperidine trifluoroacetate

HRID 1507257Notes

Reaction equation

HRID 1507257 reaction equation
[F:1][C:2]1([F:23])[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[F:23][C:2]1([F:1])[CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118207315(R)-t-butyl 3,3-difluoro-4-(4-methoxyphenyl)piperidine-1-carboxylate

Product 1

HCID 1182073723,3-Difluoro-4-(4-methoxyphenyl)piperidine trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-t-butyl 3,3-difluoro-4-(4-methoxyphenyl)piperidine-1-carboxylate (65 mg, 0.2 mmol) in DCM (0.8 mL) was added TFA (0.4 mL, 5.2 mmol) at rt. The mixture was stirred for 2 h, then concentrated to dryness in vacuo to afford crude 3,3-difluoro-4-(4-methoxyphenyl)piperidine trifluoroacetate (67.8 mg, 0.2 mmol, 100% yield), which was used in step G without further purification.

Workup

  1. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-c0140efdc13945d98cbe6477f8c9ddf1
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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