HCID 117697534, compound → HCID 117706998, compound

HRID 1778555Notes

Reaction equation

HRID 1778555 reaction equation
[F:1][C:2]1([F:23])[CH2:7][C:6]2([C:19]([O:21][CH3:22])=[O:20])[N:8](C(OCC3C=CC=CC=3)=O)[CH:3]1[CH2:4][CH2:5]2>CO.[Pd]>[F:23][C:2]1([F:1])[CH2:7][C:6]2([C:19]([O:21][CH3:22])=[O:20])[NH:8][CH:3]1[CH2:4][CH2:5]2

Participants

4

Reactant 1

HCID 117697534HCID 117697534, compound

Product 1

HCID 117706998HCID 117706998, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of O7-benzyl O4-methyl 2,2-difluoro-7-azabicyclo[2.2.1]heptane-4,7-dicarboxylate (0.24 g, 0.74 mmol), 10% Pd/C (0.3 g) in methanol (20 mL) was stirred for 12 hours under 1 atm H2. Removal of the catalyst solid and solvent gave methyl 2,2-difluoro-7-azabicyclo[2.2.1]heptane-4-carboxylate 148a. This crude product was used in next step without purification. Yield: 69.3%. MS: calc'd (MH +) 192, measured (MH +) 192.

Workup

  1. customRemoval of the catalyst solid and solvent

Sources & evidence

ORD record
ord-a987e06735b94c51a8ad03f21aa6ffba
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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