Boron trifluoride etherate → HCID 117966726, compound

HRID 712811Notes

Reaction equation

HRID 712811 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6](=O)[N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>C1COCC1>[CH3:1][C:2]1([CH3:25])[CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[C@@H:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 12052Triethylsilane2×HCID 117966886HCID 117966886, compound

Product 1

HCID 117966726HCID 117966726, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (R)-2-benzyl 1-tert-butyl 4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate (D39) (210 mg, 0.6 mmol) in THF (10 ml) cooled at −78° C., LiEt3BH 1M sol in THF (0.6 ml) was added and the mixture stirred 2 hrs at −78° C. The reaction was warmed to 0° C. and quenched with slow addition of NaHCO3 sat sol (4 ml) and 1 drop of H2O2. Stirring was continued for 20 min then THF was removed under reduced pressure and the remaining residue was taken up in water (5 ml) and extracted with DCM (3×10 ml). The organic phases were collected, dried over Na2SO4 and evaporated in vacuo. The obtained residue was dissolved in DCM (10 ml) and cooled at −78° C. under N2. Et3SiH (0.09 ml, 0.6 mmol) was added followed by addition of BF3.OEt2 (0.1 ml, 0.63 mmol) and the reaction stirred 30 min, prior further addition of Et3SiH (0.09 ml, 0.6 mmol) and BF3.OEt2 (0.1 ml, 0.63 mmol). The final reaction mixture was stirred at −78° C. for 3 hrs then quenched by the slow addition of saturated NaHCO3 and water. The reaction mixture was extracted with DCM (3×10 ml), the organic layers washed with NaCl sat sol, dried over Na2SO4 and evaporated to afford the title compound (D40) (168 mg).

Workup

  1. additionwas added
  2. temperatureThe reaction was warmed to 0° C.
  3. customquenched with slow addition of NaHCO3
  4. stirringStirring
  5. waitwas continued for 20 min
  6. customTHF was removed under reduced pressure
  7. extractionextracted with DCM (3×10 ml)
  8. customThe organic phases were collected
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuo
  11. dissolutionThe obtained residue was dissolved in DCM (10 ml)
  12. temperaturecooled at −78° C. under N2
  13. stirringthe reaction stirred 30 min
  14. customThe final reaction mixture
  15. stirringwas stirred at −78° C. for 3 hrs
  16. customthen quenched by the slow addition of saturated NaHCO3 and water
  17. extractionThe reaction mixture was extracted with DCM (3×10 ml)
  18. washthe organic layers washed with NaCl
  19. dry with materialdried over Na2SO4
  20. customevaporated

Sources & evidence

ORD record
ord-58a8a945ed32473ba4ccf2782ebd519a
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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