Toluene → HCID 11334515, compound

HRID 1671707Notes

Reaction equation

HRID 1671707 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:12][CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])O.[Na+].C1(C)C=CC=CC=1.[C:36](#[N:38])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[C:36]([C@@H:10]1[CH2:11][CH2:12][N:8]([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:9]1)#[N:38]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 86612724HCID 86612724, compound

Product 1

HCID 11334515HCID 11334515, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Conditions

Temperature
65 °C

Procedure

(3S)-1-Diphenylmethyl-3-mesyloxypyrrolidine (1.25 g) was dissolved in acetonitrile (1.75 mL). Tetrabutylammonium cyanide (1.87 g) was added to the solution, and the mixture was stirred at 65° C. for 12 hours. Saturated sodium hydrogencarbonate (7 mL) and toluene were added dropwise to the reaction mixture, whereby the organic layer was extracted. The organic layer was washed with water and then 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 (0.766 g, yield 77.4%) as colorless crystals.

Workup

  1. extractionwas extracted
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe drying agent was removed through filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto thereby yield crystals

Sources & evidence

ORD record
ord-b7ff3891a4c14ff3a707e0b5d2e1fc9e
Source dataset
uspto-grants-2011_08
Patent number
US07994344B2

Reaction notes

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