Tetrahydrofuran → HCID 66921021, compound

HRID 1487286Notes

Reaction equation

HRID 1487286 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH:10]2[O:14][CH2:15][C:16]([O:19][CH3:20])([O:17][CH3:18])[CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.C1C[O:33][CH2:32]C1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:32][OH:33])[CH:10]2[O:14][CH2:15][C:16]([O:17][CH3:18])([O:19][CH3:20])[CH:9]12)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 66921243HCID 66921243, compound

Product 1

HCID 66921021HCID 66921021, compoundYield 86%

Procedure

The olefin 1e (524 mg, 1.84 mmol) was dissolved in dry THF (70 mL), 9-BBN-H (0.5 M in THF) (7.34 mL, 3.67 mmol) was added and the solution was stirred over night. The solvent was removed by rotary evaporation and redissolved in THF (20 mL). MeOH (10 mL) was slowly added to the solution and when the gas evolution had ceased, H2O (20 mL) was added to the solution followed by NaBO3. The solution was filtered after it had been stirred for 18 hrs and the filtrate was diluted with EtOAc (70 mL) and washed with brine (2*50 mL). The organic phase was dried with Na2SO4, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (heptane: ethyl acetate 2:1) which gave the title compound (477 mg, 86%).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionredissolved in THF (20 mL)
  3. additionMeOH (10 mL) was slowly added to the solution and when the gas evolution
  4. additionH2O (20 mL) was added to the solution
  5. filtrationThe solution was filtered after it
  6. stirringhad been stirred for 18 hrs
  7. additionthe filtrate was diluted with EtOAc (70 mL)
  8. washwashed with brine (2*50 mL)
  9. dry with materialThe organic phase was dried with Na2SO4
  10. filtrationfiltered
  11. customthe solvent was evaporated in vacuo
  12. customThe crude product was purified by flash chromatography (heptane: ethyl acetate 2:1) which

Sources & evidence

ORD record
ord-c64d32dd226c49838f74b5806ca50f02
Source dataset
uspto-grants-2016_08
Patent number
US09428517B2

Reaction notes

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