Borane;tetrahydrofuran → HCID 57440706, compound

HRID 2102358Notes

Reaction equation

HRID 2102358 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 dichloromethane (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 dichloromethane (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-5fbae1bf18494a55b5985ab149ad3d0e
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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