Borane;tetrahydrofuran → HCID 18767720, compound

HRID 480128Notes

Reaction equation

HRID 480128 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[CH2:22][C:18]([C:23](O)=[O:24])([CH2:19][CH2:20][CH2:21]3)[CH2:17][CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:26])[N:3]1[CH2:27][CH2:28][CH3:29].B.C1COCC1>C1COCC1>[OH:24][CH2:23][C:18]12[CH2:22][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:26])[N:3]([CH2:27][CH2:28][CH3:29])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:15][CH2:16][CH2:17]1)[CH2:21][CH2:20][CH2:19]2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 18767705HCID 18767705, compound

Product 1

HCID 18767720HCID 18767720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.3.1]nonane 1-carboxylic acid (700 mg) was taken in THF (25 ml). BH3.THF (1M, 3.5 ml) was added and stirred at rt overnight. Next day the reaction was quenched with MeOH. Solvent was removed by rotavap. Diluted with water and extracted with ethyl acetate, washed with water, brine, dried over Na2SO4 and concentrated. Yield 690 mg. Mass (ES+ 389)

Workup

  1. customNext day the reaction was quenched with MeOH
  2. customSolvent was removed by rotavap
  3. additionDiluted with water
  4. extractionextracted with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d321a5149769431c8e9e47283d1c0016
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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