Cyanide → (S)-1-Benzyl-pyrrolidine-3-carbonitrile

HRID 639109ノート

反応式

HRID 639109 の反応式
CS(O[C@@H:6]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1)(=O)=O.[C-:18]#[N:19]>C(Cl)Cl.C(=O)(O)[O-].[Na+].O>[C:12]1([CH2:11][N:8]2[CH2:9][CH2:10][C@H:6]([C:18]#[N:19])[CH2:7]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 2

HCID 5975CyanideHCID 118072543-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

生成物 1

HCID 1515498(S)-1-Benzyl-pyrrolidine-3-carbonitrile収率 109.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
60 °C

実験手順

(3R)-1-(phenylmethyl)-3-pyrrolidinyl methanesulfonate (12.9 g, 50.6 mmol) and tertrabytulamonium cyanide (25 g, 93.3 mmol) was mixed in DCM (20 mL) and refluxed at 60° C. for 6 h. The resulting solution was cooled down to room temperature and diluted with saturated sodium bicarbonate solution in water. The aqueous phase was extracted several times with toluene. The organic fractions was combined, washed with brine and concentrated to provide the title compound as an oil (10.3 g, quantit.) which was used without further purification: LC/MS (ES) m/e 187 (M+H)+.

後処理

  1. temperatureThe resulting solution was cooled down to room temperature
  2. extractionThe aqueous phase was extracted several times with toluene
  3. washwashed with brine
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-c1228b33cbcd46bab4e694c49e7ea097
出典データセット
uspto-grants-2010_04
特許番号
US07691850B2

反応ノート

読み込み中…