Sodium Cyanide → tert-Butyl N-[3-(cyanomethyl)benzyl]-N-methylcarbamate

HRID 2228728Notes

Reaction equation

HRID 2228728 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]Br)[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C-:19]#[N:20].[Na+]>C(#N)C.[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[C:19]([CH2:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:9][N:7]([CH3:8])[C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])#[N:20]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 18470889tert-Butyl N-[3-(bromomethyl)benzyl]-N-methylcarbamate

Product 1

HCID 18470858tert-Butyl N-[3-(cyanomethyl)benzyl]-N-methylcarbamate

Reagents, catalysts & solvents 3

HCID 165294Benzyltriethylammonium bromideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl-N-[3-(bromomethyl)benzyl]-N-methylcarbamate (preparation 13) (3.2 g, 10.18 mmol) was dissolved in acetonitrile (50 ml) and treated with sodium cyanide (1.23 g, 25.10 mmol) followed by benzyl triethylammonium bromide (220 mg, 0.8 mmol) and the resultant mixture stirred at room temperature for 4 days. The resultant slurry was diluted with ethyl acetate (200 ml) washed with water, sat aq brine and dried over MgSO4. Removal of the drying agent by filtration followed by evaporation of the solvent gave a pale yellow solid which was purified by chromatography (SiO2, eluting with 100% CH2Cl2) to give the desired product with a trace of impurity (3.0 g). 1H NMR (CDCl3) δ 1.50 (s, 9H), 2.80 (s, b, 3H), 3.75 (s, 2H), 4.40 (s, 2H), 7.20 (m, 3H), 7.35 (t, 1H). LRMS m/z=278.1 (M+18)+.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customRemoval of the drying agent
  4. filtrationby filtration
  5. customfollowed by evaporation of the solvent
  6. customgave a pale yellow solid which
  7. customwas purified by chromatography (SiO2, eluting with 100% CH2Cl2)

Sources & evidence

ORD record
ord-a108a3f3508c4d0eb4dc16a544aa01a3
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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