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

HRID 129196

반응식

HRID 129196 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 1515497(R)-1-Benzyl-3-pyrrolidinecarbonitrile수율 85.6%

시약·촉매·용매 1

HCID 165872Tetrabutylammonium Cyanide촉매

반응 조건

온도
65 °C

실험 절차

(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%;

후처리

  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

출처 및 근거

ORD 기록
ord-a08583cdcccb404ba14394ae9aa4822b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466828

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