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

HRID 567805노트

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HRID 567805 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 165294Benzyltriethylammonium bromide촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-97fc98e5755f41c9973899e05c82b0ae
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180627B2

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