Sodium Cyanide → tert-Butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamate

HRID 2228774Notes

Reaction equation

HRID 2228774 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[C:1]([CH2:5][C:6]1[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=1)[CH2:9][O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])#[N:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 18470934tert-Butyl 2-{[3-(bromomethyl)benzyl]oxy}ethylcarbamate

Product 1

HCID 18470797tert-Butyl 2-{[3-(cyanomethyl)benzyl]oxy}ethylcarbamateYield 97.5%

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 6342AcetonitrileSolvent

Procedure

Sodium cyanide (284 mg, 5.78 mmol) and benzyl triethylammonium bromide (63 mg, 0.23 mmol) were added to a solution of tert-butyl 2-{[3-(bromomethyl)benzyl]oxy}ethylcarbamate (preparation 103) (798 mg, 2.31 mmol) in acetonitrile (5 ml), and the reaction stirred at room temperature for 4 days. The mixture was partitioned between water and ethyl acetate and the layers separated. The organic phase was dried over MgSO4 and evaporated under reduced pressure, to afford the desired product as an oil, (654 mg, 97%).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customthe layers separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a8207d10390247ceaa4d4fd8042624bc
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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