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

HRID 50137Notes

Reaction equation

HRID 50137 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.[C-:29]#[N:30].[Na+]>CS(C)=O.[Cl-].[Na+].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:29]#[N:30])[CH2:5]1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 69514757trans-5-Methoxymethyl-3-tosyl-Cbz-pyrrolidine

Product 1

HCID 60078795cis-5-Methoxymethyl-3-Cyano-Cbz-PyrrolidineYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

trans-5-Methoxymethyl-3-tosyl-Cbz-pyrrolidine (3.55 g, 8.8 mmol) was dissolved in DMSO (8.8 mL). Finely ground NaCN(0.65 g, 13.2 mmol) was added, and the resulting reaction mixture was stirred 4 h at 80° C. The solution was cooled to room temperature, diluted with H20 (9 mL) and brine (9 mL), and extracted with ethyl acetate. The organic extracts were dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (2/1, v/v) to afford 2.09 g (87% yield) of the desired product as an oil.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe solution was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (2/1

Sources & evidence

ORD record
ord-97c7f9063dd14d3996f8f3c303887406
Source dataset
uspto-grants-2004_03
Patent number
US06710186B2

Reaction notes

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