3a,4,5,6,7,7a-hexahydro-3H-4,7-methanoinden-5-ylamine → Tricyclo(5.2.1.0,2,6)decan-8-amine

HRID 2416991Notes

Reaction equation

HRID 2416991 reaction equation
[CH2:1]1[CH:9]2[CH:4]([CH:5]3[CH2:10][CH:8]2[CH2:7][CH:6]3[NH2:11])[CH:3]=[CH:2]1.C1C2C(C3CC2CC3N)CC=1>CO.[Pd]>[CH2:1]1[CH:9]2[CH:4]([CH:5]3[CH2:10][CH:8]2[CH2:7][CH:6]3[NH2:11])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 1052183a,4,5,6,7,7a-hexahydro-3H-4,7-methanoinden-5-ylamineHCID 130138963a,4,5,6,7,7a-Hexahydro-1H-4,7-methanoinden-5-amine

Product 1

HCID 86760Tricyclo(5.2.1.0,2,6)decan-8-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.3 g of a mixture of 3a,4,5,6,7,7a-hexahydro-1H-4,7-methanoinden-5-ylamine and 3a,4,5,6,7,7a-hexahydro-3H-4,7-methanoinden-5-ylamine (example Amine 1, a2) were dissolved in 30 ml of methanol and reduced under an atmosphere of hydrogen in the presence of 0.5 g Pd/C (10%). After 4 hours the catalyst was filtered off and washed with methanol. The filtrate was concentrated in vaccuo to give 3 g of the desired product as an oil.

Workup

  1. filtrationAfter 4 hours the catalyst was filtered off
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vaccuo

Sources & evidence

ORD record
ord-1284b9f2c39a427889a947f298a8e931
Source dataset
uspto-grants-2004_11
Patent number
US06825231B2

Reaction notes

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