Trifluoroacetic acid → HCID 86686889, compound

HRID 2363823Notes

Reaction equation

HRID 2363823 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[C:16]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:15]=2[CH3:30])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[CH3:29][O:28][C:26](=[O:27])[CH2:25][C:16]1[C:15]([CH3:30])=[C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86686891HCID 86686891, compound

Product 1

HCID 86686889HCID 86686889, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a yellow solution of (4-(7-fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.48 mmol) in dichloromethane (10 mL) was added excess trifluoroacetic acid (1.1 g, 742 μL, 9.6 mmol) at room temperature under nitrogen. The resulting dark brown solution was stirred for 2 hours at room temperature under nitrogen. The solvent was removed under vacuum and the residue (˜270 mg) was purified by flash chromatography (40 g ISCO column, 0-100% ethyl acetate/hexanes then 20% MeOH/dichloromethane) to give (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt as a light yellow solid (110 mg, 53%). MS cald. for C19H23FNO2 [(M+H)+] 316, obsd. 316.1.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue (˜270 mg) was purified by flash chromatography (40 g ISCO column, 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4c80506f985b4b52adcb8bbaf3f1a53f
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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