Boron trifluoride → HCID 67341284, compound

HRID 1671708Notes

Reaction equation

HRID 1671708 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][N:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4]1)#[N:2].[CH2:21]([Mg]Br)[CH3:22].FB(F)F.[OH-].[Na+]>O1CCCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[NH2:2][C:1]1([C@@H:3]2[CH2:7][CH2:6][N:5]([CH:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:4]2)[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 11334515HCID 11334515, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 67341284HCID 67341284, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(3R)-3-Cyano-1-(1,1-diphenylmethyl)pyrrolidine (0.70 g) was dissolved in tetrahydrofuran under an argon atmosphere. Titanium(IV) tetraisopropoxide (0.86 mL) and ethylmagnesium bromide (1.78 mL, 3 mol/L ether solution) were added to the solution at room temperature. After 05 h, trifluoroboron.diethyl ether complex (0.67 mL) was added dropwise to the mixture, and the resultant mixture was stirred at room temperature. After 18 h, 2 mol/L aqueous sodium hydroxide (30 mL) was added to the reaction mixture, and the resultant mixture was stirred for 0.25 hours. The product that precipitated was collected through filtration and then extracted. The formed aqueous layer was again extracted with ethyl acetate, and the organic layers were combined together, washed with saturated brine, and dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystals. The residue was subjected to silica gel chromatography, to thereby give the target compound (0.374 g, yield 48%).

Workup

  1. additiondiethyl ether complex (0.67 mL) was added dropwise to the mixture
  2. customThe product that precipitated
  3. filtrationwas collected through filtration
  4. extractionextracted
  5. extractionThe formed aqueous layer was again extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customThe drying agent was removed through filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto thereby yield crystals

Sources & evidence

ORD record
ord-1c8dd6bc4bb04eb197cfffa7436ef456
Source dataset
uspto-grants-2011_08
Patent number
US07994344B2

Reaction notes

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