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

HRID 567805Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567805
[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]

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 165294Benzyltriethylammonium bromideKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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, 25.10mmol) 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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-97fc98e5755f41c9973899e05c82b0ae
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180627B2

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