Borane;tetrahydrofuran → HCID 57440706, compound

HRID 600239Notes

Reaction equation

HRID 600239 reaction equation
B.O1CCCC1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][N:18]([CH2:20][CH2:21][CH3:22])[C:17](=O)[CH2:16][O:15]2)=[CH:10][C:9]=1[O:24][CH3:25]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][N:18]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:16][O:15]2)=[CH:10][C:9]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 57440705HCID 57440705, compound

Product 1

HCID 57440706HCID 57440706, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-tetrahydrofuran complex (1M in THF) (3.5 mL, 3.5 mmol) was added dropwise to a solution of the product from example 52 (0.33 g, 1.16 mmol) in dry THF (3 mL) under an atmosphere of nitrogen. The reaction mixture was refluxed for 2.5 hours then cooled and quenched by addition of methanol (1 mL). The reaction mixture was concentrated in vacuo and the residue suspended in 4N HCl (aq., 8 mL) and refluxed for 2 hours. The reaction mixture was cooled and extracted with dichloromethane (2×10 mL). The organic layers were discarded. The aqueous layer was rendered basic (pH 9-10) by addition of solid potassium carbonate before re-extracting with dichloroethane (2×15 mL). The dichloromethane extracts were washed with water (10 mL), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the title compound as an oil (0.31 g, 1.15 mmol, 99%). 1H NMR (CDCl3, 400 MHz) δ: 0.95 (t, 3H), 1.45-1.60 (m, 2H), 2.00 (t, 1H), 2.20 (t, 1H), 2.35 (t, 2H), 2.80 (d, 1H), 2.90 (d, 1H), 3.80 (t, 1H), 3.90 (s, 3H), 4.03 (dd, 1H), 4.55 (d, 1H), 6.85 (dd, 1H), 7.00 (S, 1H), 7.30 (dd, 1H). LRMS (APCI): m/z 270 (MH+).

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. temperaturethen cooled
  3. customquenched by addition of methanol (1 mL)
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. temperaturerefluxed for 2 hours
  6. temperatureThe reaction mixture was cooled
  7. extractionextracted with dichloromethane (2×10 mL)
  8. additionby addition of solid potassium carbonate
  9. extractionbefore re-extracting with dichloroethane (2×15 mL)
  10. washThe dichloromethane extracts were washed with water (10 mL)
  11. dry with materialdried over anhydrous magnesium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f5e35dccad94f1e828c0c7851542d21
Source dataset
uspto-grants-2011_03
Patent number
US07902188B2

Reaction notes

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