Potassium Cyanide → (S)-Benzyl 3-cyanopyrrolidine-1-carboxylate

HRID 50135

반응식

HRID 50135 반응식
S([C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:12]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:26]#[N:27].[K+].[Cl-].[Na+].O.O>CS(C)=O>[C:26]([C@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:12]1)#[N:27]

참가 물질

5

반응물 3

HCID 9032Potassium CyanideHCID 23713072Sodium chloride dihydrateHCID 671827093-Tosyl-Cbz-(R)-Pyrrolidine

생성물 1

HCID 44828648(S)-Benzyl 3-cyanopyrrolidine-1-carboxylate수율 70.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

3-Tosyl-Cbz-(R)-pyrrolidine (20.4 g, 0.05 mol) was dissolved in DMSO (54 mL), followed by the addition of KCN (5.3 g, 0.08 mol). The reaction mixture was stirred for 5 h at 80° C. The solution was cooled to room temperature and brine/H2O (90 mL) (1/1, v/v) was added. The aqueous solution was extracted with ethyl acetate. The organic extracts were dried over MgSO4, and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (1/1, v/v) to afford 8.13 g (65% yield) of the desired product as an oil.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes (1/1

출처 및 근거

ORD 기록
ord-2ac083ed0182438fba7129a72c857851
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710186B2

연결된 노트

불러오는 중…