Borane;tetrahydrofuran → HCID 59450539, compound

HRID 1948659Notes

Reaction equation

HRID 1948659 reaction equation
B.C1COCC1.[C:7]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH2:20][CH2:19]2)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[C:7]([O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[CH:21]([OH:25])[CH2:20][CH2:19]2)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 59450538HCID 59450538, compound

Product 1

HCID 59450539HCID 59450539, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BH3.THF (1 M solution in THF, 773.8 mL, 773.8 mmol) was added dropwise to a stirred mixture of the product of Step B (195 g, 773.8 mmol) in anhydrous THF at 0° C. under nitrogen, and the reaction mixture was stirred at rt overnight. The mixture was cooled to 0° C. and carefully quenched with methanol (500 mL). Cooling bath was removed, and the solution was stirred until bubbling stopped. The solvent was evaporated under reduce pressure. The residue was purified by column chromatography on silica gel (EtOAc:PE=1:10) to give the title compound. 1H-NMR (400 MHz, CDCl3): δ 8.19-8.22 (m, 2H), 7.62-7.66 (m, 1H), 7.52 (t, J=7.6 Hz, 2H), 7.45 (d, J=8.1 Hz, 1H), 7.06-7.10 (m, 2H), 5.25 (t, J=6.1 Hz, 1H), 3.05-3.12 (m, 1H), 2.81-2.89 (m, 1H), 2.49-2.58 (m, 1H), 1.96-2.04 (m, 2H) ppm.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customcarefully quenched with methanol (500 mL)
  3. temperatureCooling bath
  4. customwas removed
  5. stirringthe solution was stirred
  6. customuntil bubbling
  7. customThe solvent was evaporated
  8. customThe residue was purified by column chromatography on silica gel (EtOAc:PE=1:10)

Sources & evidence

ORD record
ord-376d50bdc99145a2bdaf596705c2d06e
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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