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

HRID 2228728ノート

反応式

HRID 2228728 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 165294Benzyltriethylammonium bromide触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-a108a3f3508c4d0eb4dc16a544aa01a3
出典データセット
uspto-grants-2002_07
特許番号
US06417203B1

反応ノート

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