Potassium Hydroxide → 1-Amino-4,4-difluorocyclohexanecarboxylic acid

HRID 1841884Notes

Reaction equation

HRID 1841884 reaction equation
[F:1][C:2]1([F:14])[CH2:13][CH2:12][C:5]2([NH:9]C(=O)N[C:6]2=[O:11])[CH2:4][CH2:3]1.[OH-:15].[K+]>>[NH2:9][C:5]1([C:6]([OH:15])=[O:11])[CH2:12][CH2:13][C:2]([F:14])([F:1])[CH2:3][CH2:4]1

Participants

3

Reactant 2

HCID 14797Potassium HydroxideHCID 601967718,8-Difluoro-1,3-diazaspiro[4.5]decane-2,4-dione

Product 1

HCID 470036031-Amino-4,4-difluorocyclohexanecarboxylic acid

Procedure

Under nitrogen gas, 4.10 g of the compound of Example 2A were suspended in 100 ml of 30% strength aqueous potassium hydroxide solution, and the mixture was stirred at reflux overnight. The mixture was concentrated to about 25% of the volume and, at 0-10° C., adjusted to pH 5.5 using concentrated aqueous hydrogen chloride solution. The solution was concentrated and dried. The residue (4.30 g) was used directly for the esterification.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated to about 25% of the volume and, at 0-10° C.
  3. concentrationThe solution was concentrated
  4. customdried

Sources & evidence

ORD record
ord-ec6d698679d6466d9281fbbfd848d459
Source dataset
uspto-grants-2015_02
Patent number
US08946124B2

Reaction notes

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