Trifluoroacetic acid → (1R,3R)-3-Aminocyclohexane-1-carboxylic acid 2,2,2-trifluoroacetic acid salt

HRID 1848224Notes

Reaction equation

HRID 1848224 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([OH:17])=[O:16])[CH2:10]1)=O)(C)(C)C.[C:18]([OH:24])([C:20]([F:23])([F:22])[F:21])=[O:19]>C(Cl)Cl>[F:21][C:20]([F:23])([F:22])[C:18]([OH:24])=[O:19].[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([OH:17])=[O:16])[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24720881(1R,3R)-3-(((tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 86681198(1R,3R)-3-Aminocyclohexane-1-carboxylic acid 2,2,2-trifluoroacetic acid saltYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (1R,3R)-3-((tert-butoxycarbonyl)amino)cyclohexanecarboxylic acid in a 1:1 solution of TFA: CH2Cl2 (6 mL) was stirred at rt for 3 h. The mixture was concentrated under reduced pressure. The residue was triturated in ethyl ether (50 mL) and the resulting solid was collected by filtration to afford (1R,3R)-3-aminocyclohexanecarboxylic acid trifluoroacetate (253 mg, 86%) as a white solid that did not require further purification.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe residue was triturated in ethyl ether (50 mL)
  3. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-c02c1ff4487d4af5baee0090b2082e80
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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