Borane;tetrahydrofuran → HCID 59674744, compound

HRID 1391511Notes

Reaction equation

HRID 1391511 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:18]=[CH:17][O:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.[O:20]1CCCC1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:18]=[CH:17][O:16][CH:15]=2)[CH:12]([OH:20])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuran2×HCID 53416367tert-Butyl 4-(furan-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 59674744HCID 59674744, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4 (2.33 g, 9.358 mmol) in THF (10 mL) at 0° C. borane-tetrahydrofuran, BH3-THF (28.07 mL, 28.07 mmol, 3 eq., 1M sol. in THF) was added dropwise. After stirring the reaction mixture under inert atmosphere at room temperature for 3 h, the unreacted borane was quenched by the addition of methyl alcohol (30 mL). After quenching, 3N NaOH (30 mL) was added slowly to the reaction mixture. This was followed by the addition of 30% H2O2 (15 mL). The reaction mixture was stirred under inert atmosphere at room temperature for 16 h. Solvents were removed under reduced pressure and the crude mixture was dissolved in ethyl acetate (60 mL). The ethyl acetate solution was washed with water (40 mL), bicarbonate solution (40 mL), water (40 mL), and brine (40 mL), dried over anhydrous magnesium sulfate and filtered. Removal of solvent at reduced pressure yielded the pure, white, crystalline solid 5 (2.18 g, 87%). TLC Rf=0.48 (95% CH2Cl2—MeOH); 400 MHz 1H-NMR (CDCl3) δ 1.47 (s, 9H), 1.57-1.69 (m, 1H), 1.82-1.85 (m, 0.5H), 1.86-1.88 (m, 0.5H), 2.50 (ddd, J=12.4, 10.0, 4.0 Hz, 1H), 2.62 (t, J=10.8 Hz, 1H), 2.76 (m, 1H), 3.47 (m, 1H), 4.12 (m, 1H), 4.32 (m, 1H), 6.35 (s, 1H), 7.38 (d, J=18.8 Hz, 2H); 125 MHz 13C-NMR (CDCl3) δ 14.4, 20.2, 28.6, 40.2, 60.1, 70.1, 80.1, 109.5, 126.0, 139.7, 143.6, 154.9. HRMS Calcd. for C14H21NO4Na [M++Na]: 290.1368. Found: 290.1368.

Workup

  1. customthe unreacted borane was quenched by the addition of methyl alcohol (30 mL)
  2. customAfter quenching
  3. addition3N NaOH (30 mL) was added slowly to the reaction mixture
  4. additionThis was followed by the addition of 30% H2O2 (15 mL)
  5. stirringThe reaction mixture was stirred under inert atmosphere at room temperature for 16 h
  6. customSolvents were removed under reduced pressure
  7. dissolutionthe crude mixture was dissolved in ethyl acetate (60 mL)
  8. washThe ethyl acetate solution was washed with water (40 mL), bicarbonate solution (40 mL), water (40 mL), and brine (40 mL)
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customRemoval of solvent at reduced pressure

Sources & evidence

ORD record
ord-ca8f2fb5ba3c4e57b9a24100715b61c9
Source dataset
uspto-grants-2008_03
Patent number
US07338965B2

Reaction notes

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