Ammonium formate → Methyl 2-adamantylacetate

HRID 1925520Notes

Reaction equation

HRID 1925520 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[CH:11][C:12]([O:14][CH3:15])=[O:13])[CH2:8]2.C([O-])=O.[NH4+]>CO.[Pd]>[CH:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]([CH2:8]3)[CH:2]1[CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:4]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 13448912Methyl tricyclo[3.3.1.13,7]dec-2-ylideneacetate

Product 1

HCID 54117306Methyl 2-adamantylacetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Intermediate 71 (6.4 g, 31.07 mmol) in methanol (100 mL) was added ammonium formiate (7.8 g, 124.33 mmol), then under argon was added palladium on charcoal (0.6 g, 10%). The reaction mixture was stirred at room temperature for 3 hours. The catalyst was filtered through Celite® and the solvent removed under reduced pressure. The crude was treated with water and ethyl acetate, and the organic layer was extracted and the solvent was removed under reduced pressure. The title compound was obtained as an colourless iol (6.2 g, 95%).

Workup

  1. filtrationThe catalyst was filtered through Celite®
  2. customthe solvent removed under reduced pressure
  3. additionThe crude was treated with water and ethyl acetate
  4. extractionthe organic layer was extracted
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c4414b81616d4ce693c3c7d7a87eb556
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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