HCID 131734835, compound → HCID 117706992, compound

HRID 1778562Notes

Reaction equation

HRID 1778562 reaction equation
[F:1][C:2]1([F:24])[CH2:7][CH:6]2[N:8](C(OCC3C=CC=CC=3)=O)[CH:3]1[CH2:4][C@H:5]2[C:19]([O:21][CH2:22]C)=[O:20]>CO.[Pd]>[F:24][C:2]1([F:1])[CH2:7][CH:6]2[NH:8][CH:3]1[CH2:4][CH:5]2[C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 1

HCID 131734835HCID 131734835, compound

Product 1

HCID 117706992HCID 117706992, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of O7-benzyl O5-ethyl (5R)-2,2-difluoro-7-azabicyclo[2.2.1]heptane-5,7-dicarboxylate (0.33 g, 1.0 mmol), 10% Pd/C (0.4 g) in methanol (20 mL) was stirred for 24 hours at 1 atm of H2. Removal of catalyst and solvent afforded crude methyl 2,2-difluoro-7-azabicyclo[2.2.1]heptane-5-carboxylate 151a, which was used in next step without purification. Yield: 100%. MS: calc'd (MH +) 192, measured (MH +) 192.

Workup

  1. customRemoval of catalyst and solvent

Sources & evidence

ORD record
ord-0d79a862b09748efb3f472b80390f37c
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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