Acetonitrile → (R)-1-Benzyl-3-pyrrolidinecarbonitrile

HRID 129196

反応式

HRID 129196 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[C:23](#[N:25])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:23]#[N:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidine

生成物 1

HCID 1515497(R)-1-Benzyl-3-pyrrolidinecarbonitrile収率 85.6%

試薬・触媒・溶媒 1

HCID 165872Tetrabutylammonium Cyanide触媒

反応条件

温度
65 °C

実験手順

(S)-1-Benzyl-3-mesyloxypyrrolidine (264.3 g, 1.03 mol) was dissolved in acetonitrile (170 mL) and tetrabutylammonium cyanide (556 g, 2.07 mol) was added. The resulting mixture was heated at 65° C. for 2 days and then cooled to room temperature and saturated NaHCO3 (500 mL) added. The organic layer was separated and the aqueous layer extracted with toluene (600 mL and 400 mL). The combined organic layers were washed with water (4×500 mL) and concentrated under reduced pressure to give (R)-1-benzyl-3-cyanopyrrolidine as a brown oil (165 g, 85.6%): IR: 2239 cm-1 ; VPC: 97.0%;

後処理

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with toluene (600 mL and 400 mL)
  4. washThe combined organic layers were washed with water (4×500 mL)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a08583cdcccb404ba14394ae9aa4822b
出典データセット
uspto-grants-1995_11
特許番号
US05466828

関連ノート

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