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

HRID 567845Notes

Reaction equation

HRID 567845 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-c81997e3d89745679dc2ad754751fa44
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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