1,4-Dioxane → HCID 18391977, compound

HRID 618183Notes

Reaction equation

HRID 618183 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][N:11](Cl)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:27]#[N:28])(C)C.O1CCOCC1>[I-].[Zn+2].[I-].O>[CH2:1]([O:8][C@H:9]1[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][NH:11][CH:10]1[C:27]#[N:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 82115Trimethylsilyl cyanideHCID 54050595HCID 54050595, compound

Product 1

HCID 18391977HCID 18391977, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolvent2×

Procedure

To the toluene solution was added zinc iodide (0.5 g) and trimethylsilyl cyanide (20 ml, 160 mmol). The mixture was stirred at room temperature for 20 hours under a nitrogen atmosphere. Dioxan (5 ml) and water (5 ml) were added and stirring was continued for 11/2 hour at room temperature. Water (150 ml) was added, the organic phase isolated and washed with water (200 ml), dried with magnesium sulphate and evaporated to dryness in vacuo to give the title compound as an oil. Purification of the crude product on a silica gel column (Eluent: ethyl acetate) afforded (3R,4R)-3,4-dibenzyloxy-pyrrolidine-2-carbonitrile (13.5 g, yield: 82% overall) as an oil.

Workup

  1. stirringstirring
  2. custom2 hour
  3. customat room temperature
  4. customthe organic phase isolated
  5. washwashed with water (200 ml)
  6. dry with materialdried with magnesium sulphate
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-8dfa3ab5cd464c1ea96cb8c940521e7c
Source dataset
uspto-grants-1999_09
Patent number
US05952363

Reaction notes

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