Ammonia → N-[4-(aminomethyl)phenyl]-alpha(R)-hydroxy-3-oxo-4-[4-(trifluoromethyl)phenyl]-2(R)-morpholineacetamide

HRID 237319Notes

Reaction equation

HRID 237319 reaction equation
C([O:4][C@H:5]([C@H:9]1[O:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[C:10]1=[O:25])[C:6](O)=[O:7])(=O)C.[H][H].[NH3:28]>CO.[Ni]>[NH2:28][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([NH:11][C:6](=[O:7])[C@H:5]([OH:4])[C@H:9]2[O:14][CH2:13][CH2:12][N:11]([C:15]3[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:20]=3)[C:10]2=[O:25])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 58181429(R)-2-acetoxy-2-((R)-3-oxo-4-(4-(trifluoromethyl)phenyl)morpholin-2-yl)acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 58181437N-[4-(aminomethyl)phenyl]-alpha(R)-hydroxy-3-oxo-4-[4-(trifluoromethyl)phenyl]-2(R)-morpholineacetamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To Compound 99-1 in 15 mL of 7M NH3 in MeOH was added excess Raney Ni (an aq. suspension) and the mixture stirred under a balloon of hydrogen for two hours. The mixture was filtered and evaporated to dryness yielding a white solid. Purification by RP-HPLC yielded 34 mg of EXAMPLE 99 as a white solid after conversion to the HCl salt by the addition of 1N HCl in diethyl ether and evaporation to dryness.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. customyielding a white solid
  4. customPurification by RP-HPLC

Sources & evidence

ORD record
ord-edc2a7be543349599d6f8e00413e0824
Source dataset
uspto-grants-2014_02
Patent number
US08642582B2

Reaction notes

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