HCID 117698034, compound → HCID 117697917, compound

HRID 1778536Notes

Reaction equation

HRID 1778536 reaction equation
C([N:8]1[CH:13]2[C:14]([F:17])([F:16])[CH2:15][CH:9]1[CH2:10][C:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([OH:18])[CH2:12]2)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[F:17][C:14]1([F:16])[CH2:15][CH:9]2[NH:8][CH:13]1[CH2:12][C:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([OH:18])[CH2:10]2

Participants

5

Reactant 2

HCID 117698034HCID 117698034, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117697917HCID 117697917, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Step VIIII: A mixture of compound 116i (340 mg, 1 mmol, 1.0 eq) and Pd(OH)2/C (100 mg, 30%) in MeOH (20 mL) was stirred at room temperature for 16 h under 1 atmosphere of hydrogen. The mixture was filtered, and the filtrate was concentrated to give ethyl 2-(6,6-difluoro-3-hydroxy-8-azabicyclo[3.2.1]octan-3-yl)acetate 116a as a colorless oil, 224 mg, yield: 90%. MS: calc'd (MH+) 250, measured (MH+) 250.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-88f4e509bff0464aa19c60edc8b959b4
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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