Trifluoroacetic acid → HCID 86686887, compound

HRID 2363814Notes

Reaction equation

HRID 2363814 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=3)[CH:24]=[C:23]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:36][O:35][C:33](=[O:34])[CH2:32][C:23]1[CH:22]=[C:21]([CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866868864-(7-Fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86686887HCID 86686887, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.9 mL, 38 mmol) was added at 0° C. to a stirred solution of 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (which may be prepared as described above; 1.05 g, 2.6 mmol) in dry CH2Cl2 (25 mL) under nitrogen. The solution was stirred at room temperature for 16 h and then the solvent was evaporated under reduced pressure. The residue was triturated with diethyl ether (3×5 mL) and dried under vacuum to give (6-fluoro-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (0.80 g, 74%) as a white solid. MS cald. for C18H21FNO2 [(M+H)+] 302, obsd. 302.4.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was triturated with diethyl ether (3×5 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4cba156755bc4a24b198cff2c6883f6a
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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