Potassium Cyanide → HCID 67344654, compound

HRID 1020931Notes

Reaction equation

HRID 1020931 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:17]#[N:18].[K+].C1OCCOCCOCCOCCOCCOC1.[Si:38](C#N)([CH3:41])([CH3:40])[CH3:39].C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([C:17]#[N:18])([O:16][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 5612031-N-Cbz-3-pyrrolidinone

Product 1

HCID 67344654HCID 67344654, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cold solution of 3-Oxo-pyrrolidine-1-carboxylic acid benzyl ester 1a (250 g, 1.14 mol) in 3.5 L anhydrous dichloromethane was added KCN (7.5 g, 0.12 mol), followed by 18-crown-6 (30 g, 0.11 mol), though not completely dissolved, was added TMSCN (183 mL, 1.37 mol) slowly over a period of 20 min. The reaction was stirred at ambient temperature for 1 overnight. A semi-saturated NaHCO3 solution (2 L) was added at 15° C., stirred for 10 min and then the organic layer was separated, dried over magnesium sulfate, filtered and evaporated to give 3-Cyano-3-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester 2a, 422 g (>100%).

Workup

  1. dissolutionthough not completely dissolved
  2. stirringstirred for 10 min
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-76265b5fc10541a8ac95efa091013fea
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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