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

HRID 1466445Notes

Reaction equation

HRID 1466445 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-9068a503b04945deac0afd7308480af9
Source dataset
uspto-grants-2015_04
Patent number
US09000026B2

Reaction notes

Loading…