Lithium Hydroxide → HCID 20600665, compound

HRID 2105645Notes

Reaction equation

HRID 2105645 reaction equation
N[C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[C:27]([O:32]C)(=[O:31])[C@@H:28]([CH3:30])[OH:29].N(OCCC(C)C)=O.[Li+].[OH-]>O.CO>[O:23]=[C:14]1[N:13]([CH2:24][CH2:25][CH3:26])[C:12]2[N:11]=[C:10]([C:5]34[CH2:6][CH2:7][C:2]([O:29][C@H:28]([CH3:30])[C:27]([OH:32])=[O:31])([CH2:9][CH2:8]3)[CH2:3][CH2:4]4)[NH:18][C:17]=2[C:16](=[O:19])[N:15]1[CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8053Isoamyl NitriteHCID 637514(+)-Methyl lactateHCID 18767683HCID 18767683, compound

Product 1

HCID 20600665HCID 20600665, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

8-(4-Amino-bicyclo[2.2.2]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (Example 20) (0.100 g. 0.279 mmol) was combined with 1.5 ml of (R)-methyl lactate and 0.075 ml of isoamyl nitrite. The mixture was heated to 60° C. for 2 h and cooled to rt. The reaction mixture was conc'd in vacuo and the residue was stirred with 8 ml of a 50% MeOH solution and 0.050 g LiOH overnight. The reaction mixture was conc'd in vacuo, taken up in 8 ml of water, the pH of the solution was adjusted to 10 and the mixture extracted twice with 6-ml portions of CH2Cl2. The water layer was acidified with conc'd HCl and the resultant precipitate collected by suction filtration to give 0.024 g (20% yield). (MH+=433.08)

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture extracted twice with 6-ml portions of CH2Cl2
  3. filtrationthe resultant precipitate collected by suction filtration
  4. customto give 0.024 g (20% yield)

Sources & evidence

ORD record
ord-4982a2d66f704aadae59cd1a76f5f975
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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