Potassium Cyanide → cis-5-Methoxymethyl-3-Cyano-Cbz-Pyrrolidine

HRID 50140Notes

Reaction equation

HRID 50140 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[N:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:7][C@@H:6](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:5]1.C1OCCOCCOCCOCCOCCOC1.[C-:47]#[N:48].[K+]>CS(C)=O.O>[CH3:1][O:2][CH2:3][C@H:4]1[N:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:7][C@@H:6]([C:47]#[N:48])[CH2:5]1

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 69514757trans-5-Methoxymethyl-3-tosyl-Cbz-pyrrolidine

Product 1

HCID 60078795cis-5-Methoxymethyl-3-Cyano-Cbz-PyrrolidineYield 69%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5 (13.76 g, 0.034 mol) was dissolved in DMSO (17 mL). 18-Crown-6 (5 eq) and finely ground KCN (5 eq) were added and the reaction mixture was stirred for 6 h at 80° C. The reaction solution was diluted with H2O (17 mL) and then extracted with ethyl acetate. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (4/1, v/v) to afford 13.76 g (69% yield) of the desired product 6 as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography
  5. washeluting with hexanes/ethyl acetate (4/1

Sources & evidence

ORD record
ord-387de7f4fa9a44198c1451ccf90ced71
Source dataset
uspto-grants-2004_03
Patent number
US06710186B2

Reaction notes

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