HCID 58930097, compound → HCID 58929618, compound

HRID 46104Notes

Reaction equation

HRID 46104 reaction equation
C([O:8][C@H:9]1[CH2:14][C@H:13]2[CH2:15][C@@H:10]1[CH2:11][C:12]2([F:17])[F:16])C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:16][C:12]1([F:17])[CH2:11][C@H:10]2[CH2:15][C@@H:13]1[CH2:14][C@@H:9]2[OH:8]

Participants

5

Reactant 2

HCID 58930097HCID 58930097, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58929618HCID 58929618, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium (10 wt. % on activated carbon, 0.28 g) was added to a solution of (1R,4R,5S)-5-(benzyloxy)-2,2-difluorobicyclo[2.2.1]-heptane (1.43 g, 6.0 mmol) in methanol (15 mL), and the mixture was placed under a balloon full of hydrogen.After stirring at ambient temperature for 4 h, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo. The residue was adsorbed onto a small pad of silica gel, and eluted with 20% of ethyl acetate in hexanes. The solvents were removed in vacuo to give the title compound as a white solid.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. washeluted with 20% of ethyl acetate in hexanes
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-f9b90af4e6164346a923d58c98387335
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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