Methanol → HCID 21309686, compound

HRID 1416613Notes

Reaction equation

HRID 1416613 reaction equation
Cl.Cl.[CH3:3][O:4][C@H:5]1[CH2:9][N:8]([CH3:10])[C@H:7]([CH2:11][O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:6]1.CO>C1COCC1>[CH3:3][O:4][CH:5]1[CH2:9][N:8]([CH3:10])[C@H:7]([CH2:11][O:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 887MethanolHCID 67586680HCID 67586680, compound

Product 1

HCID 21309686HCID 21309686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the compound from step 47a above, dissolved in 4 mL of THF, was added 3.39 mL of BH3 and the mixture was heated at reflux for 2 hours. Methanol was added to the reaction mixture and evaporated. The residue was dissolved in anhydrous ethanol. Cesium fluoride was added, and the resultant solution was stirred under reflux for 16 hr. Evaporation of the solvent provided a white solid which was purified on a silica gel column. MS (DCI/NH3) m/e: 223 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.34 (m, 1H), 8.23 (t, J=3 Hz, 1H), 7.22 (m, 1H), 3.93-4.10 (m, 3H), 3.44-3.54 (m, 1H), 3.32 (s, 3H), 3.03-2.87 (m, IF), 2.51 (s, 3H), 2.44-2.33 (m, 11H), 2.11-1.92 (m, 2H).

Workup

  1. additionwas added 3.39 mL of BH3
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 hours
  4. customevaporated
  5. dissolutionThe residue was dissolved in anhydrous ethanol
  6. additionCesium fluoride was added
  7. temperatureunder reflux for 16 hr
  8. customEvaporation of the solvent
  9. customprovided a white solid which
  10. customwas purified on a silica gel column

Sources & evidence

ORD record
ord-070b1aee5cad4d39a545eeb81e1ccaf7
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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