Hydrochloric Acid → (2S,3S)-2-Phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidine

HRID 2269246Notes

Reaction equation

HRID 2269246 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([CH:22]([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])[CH:19]=[CH:18][C:17]=2[O:31][CH3:32])[C@@H:9]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O>[C:33]1([C@H:9]2[C@@H:10]([NH:14][CH2:15][C:16]3[CH:21]=[C:20]([CH:22]([C:27]([F:28])([F:29])[F:30])[C:23]([F:24])([F:25])[F:26])[CH:19]=[CH:18][C:17]=3[O:31][CH3:32])[CH2:11][CH2:12][CH2:13][NH:8]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15549735(2S, 3S)-1-tert-Butoxycarbonyl-2-phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidine

Product 1

HCID 15549736(2S,3S)-2-Phenyl-3-(5-(2,2,2-trifluoro-1-(trifluoromethyl)ethyl)-2-methoxybenzyl)aminopiperidineYield 115.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 13 (170 mg) in AcOEt (6 ml) was added conc. HCl (1 ml). The mixture was stirred at room temperature for 45 minutes. The mixture was poured into NaHCO3 aq., and extracted with CH2Cl2. The combined extracts were dried (Na2SO4), and concentrated in vacuo to give Compound 14 (160 mg) as a yellow oil.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b57afab2572f436ba4f978fbd4052e25
Source dataset
uspto-grants-2001_12
Patent number
US06329396B1

Reaction notes

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