HCID 22020358, compound → Decahydro-2-trifluoromethyl-1,4-methanonaphthalene

HRID 2114533Notes

Reaction equation

HRID 2114533 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]1[CH2:12][CH:11]2[CH2:13][CH:4]1[C:5]1[CH:10]2[CH2:9][CH2:8][CH2:7][CH:6]=1.[H][H]>[Pd].CO>[F:1][C:2]([F:14])([F:15])[CH:3]1[CH2:12][CH:11]2[CH2:13][CH:4]1[CH:5]1[CH:10]2[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 22020358HCID 22020358, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22020359Decahydro-2-trifluoromethyl-1,4-methanonaphthalene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 400 ml autoclave is charged with 177 g of the thus purified octahydro-2-trifluormethyl-1,4-methanonaphthalene, methanol (100 ml, Burdick & Jackson, HPLC grade), and palladium on activated carbon (1.5 g containing 10% Pd, Alfa products, powder). The autoclave is closed and sealed, then it is shaken under 50 psig hydrogen pressure for 20 minutes at room temperature. The hydrogen pressure is increased to 200 psig for 10 minutes at room temperature followed by 600 psig at 70° C. for 45 minutes. The decahydro-2-trifluormethyl-1,4-methanonaphthalene product is purified by distillation at reduced pressure. The distilled product is then treated with concentrated sulfuric acid followed by silica gel treatment similar to what described in the example 2.

Workup

  1. customThe autoclave is closed
  2. customsealed
  3. distillationThe decahydro-2-trifluormethyl-1,4-methanonaphthalene product is purified by distillation at reduced pressure
  4. additionThe distilled product is then treated with concentrated sulfuric acid

Sources & evidence

ORD record
ord-d1ca5809758445d1aedb96a331d6261a
Source dataset
uspto-grants-2008_10
Patent number
US07435528B2

Reaction notes

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