Pyridine → 3-Benzyloxy-a-(N-butyryl)-aminopropionitrile

HRID 1874873ノート

反応式

HRID 1874873 の反応式
[CH2:1]([O:8][CH2:9][CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#[N:13].[Na+].[Cl-].[NH4+].[N:17]1[CH:22]=CC=CC=1.[C:23](Cl)(=[O:27])[CH2:24][CH2:25][CH3:26]>[OH-].[NH4+].O>[C:22]([CH:10]([NH:13][C:23](=[O:27])[CH2:24][CH2:25][CH3:26])[CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)#[N:17]

参加物

8

反応物 5

HCID 1049PyridineHCID 8855Butyryl chlorideHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 108989(Phenylmethoxy)acetaldehyde

生成物 1

HCID 594513703-Benzyloxy-a-(N-butyryl)-aminopropionitrile収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 14923Ammonium Hydroxide溶媒

実験手順

Benzyloxyacetaldehyde (1.5 g, 10.0 mmol) was added dropwise to a stirred solution of sodium cyanide (0.61 g, 12.4 mmol) and ammonium chloride (0.79 g, 14.8 mmol) in 25% ammonium hydroxide (5 mL). The solution was stirred at RT for 48 h, then extracted with CH2Cl2 (20 mL). The organic extract was washed with brine, dried (Na2SO4) and filtered. The filtrate was cooled to 0° C., and pyridine (1.3 mL, 16.1 mmol) was added followed by butyryl chloride (1.56 mL, 15.0 mmol). The reaction mixture was stirred for 2 h at 0° C. Water was added (10 mL) and the organic phase was separated, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel flash column chromatography (5-35% EtOAc:hexanes) to give the title compound (1.99 g, 81%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.32-7.43 (m, 5H), 6.09 (d, 1H), 5.08-5.14 (m, 1H), 4.64 (ABq, 2H), 3.71 (ABq, 2H), 2.20 (t, 2H), 1.62-1.73 (m, 2H), 0.96 (t, 3H). ES-LCMS: m/z 247.2 (M+1).

後処理

  1. extractionextracted with CH2Cl2 (20 mL)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. temperatureThe filtrate was cooled to 0° C.
  7. stirringThe reaction mixture was stirred for 2 h at 0° C
  8. customthe organic phase was separated
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel flash column chromatography (5-35% EtOAc:hexanes)

出典と根拠

ORDレコード
ord-3c45d961c0594ba99ee5c712d3e4d610
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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