Ethyl{7-[5-(2-methyl-propenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-yl}carbamate → Ethyl[7-(5-isobutylpyridin-2-yl)-7-azaspiro[3.5]non-2-yl]carbamate

HRID 336559Notes

Reaction equation

HRID 336559 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[NH:5][CH:6]1[CH2:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([CH:21]=[C:22]([CH3:24])[CH3:23])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[CH2:7]1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[NH:5][CH:6]1[CH2:9][C:8]2([CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:17][N:16]=3)[CH2:13][CH2:14]2)[CH2:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 131732014Ethyl{7-[5-(2-methyl-propenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-yl}carbamate

Product 1

HCID 131732016Ethyl[7-(5-isobutylpyridin-2-yl)-7-azaspiro[3.5]non-2-yl]carbamateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.05 g (0.45 mmol) of palladium-on-charcoal is added to a solution of 0.37 g (1.08 mmol) of ethyl{7-[5-(2-methylpropenyl)pyridin-2-yl]-7-azaspiro[3.5]non-2-yl}carbamate obtained in the preceding step, in 15 mL of methanol. The reaction medium is placed in a Parr flask under a hydrogen atmosphere (10 psi) at room temperature for 2 hours. The resulting mixture is filtered through a Büchner funnel and the filtrate is then concentrated under reduced pressure. 0.37 g of expected product is thus obtained in the form of a yellow wax.

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. filtrationThe resulting mixture is filtered through a Büchner funnel
  4. concentrationthe filtrate is then concentrated under reduced pressure

Sources & evidence

ORD record
ord-19eb4278f24c455380699eb73b428866
Source dataset
uspto-grants-2014_11
Patent number
US08889702B2

Reaction notes

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