Lithium borohydride → HCID 70656103, compound

HRID 2401326Notes

Reaction equation

HRID 2401326 reaction equation
C[O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]3[NH:21][C:20]4[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17](=[O:26])[NH:16][C:15]=4[N:14]=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=O.[BH4-].[Li+]>C1COCC1.CO>[OH:2][CH2:3][C:5]12[CH2:10][CH2:9][C:8]([C:13]3[NH:21][C:20]4[C:19](=[O:22])[N:18]([CH2:23][CH2:24][CH3:25])[C:17](=[O:26])[NH:16][C:15]=4[N:14]=3)([CH2:11][CH2:12]1)[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 67195727HCID 67195727, compound

Product 1

HCID 70656103HCID 70656103, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2,6-dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (2.4 g, 0.006 moles) in THF (35 ml), methanol (0.4 ml) was added. To this mixture, lithium borohydride (1.45 g, 0.066 mole) was added slowly and refluxed overnight. Reaction mixture was concentrated under reduced pressure and quenched with 1N HCl. Water was added to the residue and extracted with ethyl acetate. Organic layer was dried over anhydrous sodium sulphate and concentrated under vacuum.

Workup

  1. temperaturerefluxed overnight
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customquenched with 1N HCl
  5. additionWater was added to the residue
  6. extractionextracted with ethyl acetate
  7. dry with materialOrganic layer was dried over anhydrous sodium sulphate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4a10d48e311445c2894b60bbeff6de50
Source dataset
uspto-grants-2014_08
Patent number
US08796290B2

Reaction notes

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