Borane;tetrahydrofuran → HCID 117653560, compound

HRID 1486517Notes

Reaction equation

HRID 1486517 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][CH2:23][C:24](O)=[O:25])=[C:20]([CH3:29])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:30])[CH3:2].B.C1COCC1>C1COCC1>[OH:25][CH2:24][CH2:23][O:22][C:21]1[CH:27]=[CH:28][C:18]([C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:31])=[C:8]([CH3:30])[CH:9]=2)([CH2:14][CH3:15])[CH2:16][CH3:17])=[CH:19][C:20]=1[CH3:29]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 117653526HCID 117653526, compound

Product 1

HCID 117653560HCID 117653560, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of compound 4 (59.7 mg, 0.1393 mmol) in THF (1.25 mL) at −10° C. was added BH3•THF (140 μL of a 1.0 M solution in THF, 0.1393 mmol, 1.0 equiv.) and the resulting solution was warmed to RT and stirred for 16 h. the reaction was cooled to 0° C. and a further portion of BH3 THF (140 μL of a 1.0 M solution in THF, 0.1393 mmol, 1.0 equiv.) was added. After warming to RT and stirring for 3 h, the reaction was re-cooled to 0° C. and quenched by the addition of H2O and K2CO3 (ca. 20 mg). The resulting mixture was warmed to RT, diluted with H2O and extracted with Et2O (×4). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to afford a colourless oil which was purified by column chromatography (5:20:75 MeOH/EtOAc/hexanes) to afford the title compound 11 (52.4 mg, 91%)

Workup

  1. temperaturewas cooled to 0° C.
  2. temperatureAfter warming to RT
  3. stirringstirring for 3 h
  4. temperaturethe reaction was re-cooled to 0° C.
  5. customquenched by the addition of H2O and K2CO3 (ca. 20 mg)
  6. temperatureThe resulting mixture was warmed to RT
  7. additiondiluted with H2O
  8. extractionextracted with Et2O (×4)
  9. dry with materialThe combined organic extracts were dried over MgSO4
  10. concentrationconcentrated in vacuo
  11. customto afford a colourless oil which
  12. customwas purified by column chromatography (5:20:75 MeOH/EtOAc/hexanes)

Sources & evidence

ORD record
ord-5358e414f7bf4f6cb2150d8950fa8879
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

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