3-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester → 3-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

HRID 1793818Notes

Reaction equation

HRID 1793818 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH:4]=[CH:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20](=[O:23])[NH:19][C:18](=[O:24])[N:17]([CH2:25][CH2:26][CH3:27])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]12[CH2:11][CH2:10][C:9]([C:14]3[NH:22][C:21]4[C:20](=[O:23])[NH:19][C:18](=[O:24])[N:17]([CH2:25][CH2:26][CH3:27])[C:16]=4[N:15]=3)([CH2:8][CH2:7]1)[CH2:12][CH2:13]2

Participants

4

Reactant 1

HCID 691483283-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester

Product 1

HCID 213520793-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl esterYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acrylic acid methyl ester (300 mg) was dissolved in 20 mL of THF. 10% Pd on C (25 mg) was added and the resulting reaction mixture was hydrogenated under 50 psi of H2 at rt for 6 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure to afford 280 mg of the desired product.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce9315157eec419f96c9f7f424271881
Source dataset
uspto-grants-2006_04
Patent number
US07022686B2

Reaction notes

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