Borane;tetrahydrofuran → HCID 11994549, compound

HRID 395280Notes

Reaction equation

HRID 395280 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([C:22](O)=[O:23])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:25])[NH:3]1.B.C1COCC1>C1COCC1>[OH:23][CH2:22][C:17]12[CH2:18][CH2:19][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:25])[NH:3][C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:21][CH2:20]1)[CH2:15][CH2:16]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 22219469HCID 22219469, compound

Product 1

HCID 11994549HCID 11994549, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-(2,6-Dioxo-3-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid (3.2 g, 9.25 mmol) was dissolved in 100 mL of anhydrous THF and cooled to 0° C. Borane-THF (1.0 M in THF, 18.5 mL, 2 eq) was added and the reaction mixture was stirred at 0° C. for 10 min, then warmed to rt and stirred for 48 h. The reaction mixture was then carefully quenched with 10 mL of MeOH and then concentrated under reduced pressure. The resulting residue was dissolved in 20 mL of MeOH and concentrated under reduced pressure. This treatment was repeated four more times to afford the desired alcohol.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred for 48 h
  3. customThe reaction mixture was then carefully quenched with 10 mL of MeOH
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in 20 mL of MeOH
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40f295149812466f8490dae37a200f7a
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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