Borane → HCID 69523344, compound

HRID 968770Notes

Reaction equation

HRID 968770 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12](=O)[C@@H:13]([NH2:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1.B>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[F:25])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][C@@H:13]([NH2:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 69523102HCID 69523102, compound

Product 1

HCID 69523344HCID 69523344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

The product from Example 20, step b) (0.544 g) was dissolved in THF (5 ml) and borane [10.05 ml (1M in THF)] was added. The reaction was heated at reflux for 2 hours. The reaction was quenched slowly with MeOH and the solvents evaporated. Aqueous HCl (5 ml Concentrated HCl: 5 ml H2O) was added and the reaction heated at 70° C. for 1 hour. NaOH (2M) was added until pH 9 was reached. The product was extracted with CH2Cl2 and the combined organics washed with saturated aqueous NaHCO3, dried with Na2SO4 and solvents evaporated. Purification by flash chromatography (dichloromethane:methanol: 880 NH3 (aq) 89:10:1)gave the sub-title compound as an oil (0.377 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 hours
  3. customThe reaction was quenched slowly with MeOH
  4. customthe solvents evaporated
  5. additionAqueous HCl (5 ml Concentrated HCl: 5 ml H2O) was added
  6. additionNaOH (2M) was added until pH 9
  7. extractionThe product was extracted with CH2Cl2
  8. washthe combined organics washed with saturated aqueous NaHCO3
  9. dry with materialdried with Na2SO4 and solvents
  10. customevaporated
  11. customPurification by flash chromatography (dichloromethane

Sources & evidence

ORD record
ord-5f603ef23af749faab2a53c2843c23a0
Source dataset
uspto-grants-2007_12
Patent number
US07304077B2

Reaction notes

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