Sodium Cyanide → 1-Benzylpyrrolidine-3-carbonitrile

HRID 491510ノート

反応式

HRID 491510 の反応式
S([O-])(=O)(=O)C.[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15](O)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C-:19]#[N:20].[Na+]>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH2:6]([N:13]1[CH2:17][CH2:16][CH:15]([C:19]#[N:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 8929Sodium CyanideHCID 69889N-benzyl-3-pyrrolidinolHCID 85257Methanesulfonate

生成物 1

HCID 46745791-Benzylpyrrolidine-3-carbonitrile収率 75.7%

試薬・触媒・溶媒 2

HCID 165872Tetrabutylammonium Cyanide触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
82.5 °C

実験手順

This transformation was carried out using the method described in C. Thomas et. al. reference 97. The mesylate of racemic 1-benzyl-pyrrolidin-3-ol (0.039 mol, 10 g), prepared as described above, sodium cyanide (0.24 mol, 15 g) and tetrabutylammonium cyanide (10 g, 0.037 mol) in 75 mL of DMSO was stirred at 80-85° C. for 16 h. The reaction mixture was partitioned between diethyl ether and sat. aq sodium bicarbonate. The aqueous layer was extracted twice with ether and the combined organic layer was washed successively with sodium bicarbonate, water, and sat aq. NaCl. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and purified by flash chromatography over silica gel using a gradient of 20 to 30% ethyl acetate in hexane to afford 5.5 g of the desired product.

後処理

  1. customThe reaction mixture was partitioned between diethyl ether and sat. aq sodium bicarbonate
  2. extractionThe aqueous layer was extracted twice with ether
  3. washthe combined organic layer was washed successively with sodium bicarbonate, water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. custompurified by flash chromatography over silica gel using a gradient of 20 to 30% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-178c84c80efa45d59f6e2a8c7ccc7419
出典データセット
uspto-grants-2009_05
特許番号
US07531552B2

反応ノート

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