Hydrochloric Acid → 1-Amino-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylic acid

HRID 922125Notes

Reaction equation

HRID 922125 reaction equation
[CH3:1][O:2][C:3]1([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13][C:6]2([NH:10]C(=O)N[C:7]2=[O:12])[CH2:5][CH2:4]1.Cl.[OH-:20].[Na+]>>[NH2:10][C:6]1([C:7]([OH:12])=[O:20])[CH2:5][CH2:4][C:3]([O:2][CH3:1])([C:15]([F:18])([F:17])[F:16])[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 712474398-Methoxy-8-(trifluoromethyl)-1,3-diazaspiro[4.5]decane-2,4-dione

Product 1

HCID 904137291-Amino-4-methoxy-4-(trifluoromethyl)cyclohexanecarboxylic acid

Procedure

10.00 g (37.56 mmol) of 8-methoxy-8-(trifluoromethyl)-1,3-diazaspiro[4.5]decane-2,4-dione (Example 14A) were suspended in 125 ml of 3-molar aqueous sodium hydroxide solution and stirred under reflux conditions for 3 days. Subsequently, the pH was adjusted to 6 using concentrated aqueous hydrochloric acid, and the precipitated product was filtered off, washed with water and dried under reduced pressure. This gave 12.20 g (135% of theory; the product contains inorganic salts) of the title compound as a white powder.

Workup

  1. filtrationthe precipitated product was filtered off
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-d020708915d04aff8b5bf3372990318e
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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