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Potassium Cyanide → cis-5-Methoxymethyl-3-Cyano-Cbz-Pyrrolidine

HRID 50140
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HRID 50140 반응식
[CH3:1][O:2][CH2:3][C@@H:4]1[N:8]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:7][C@@H:6](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:5]1.C1OCCOCCOCCOCCOCCOC1.[C-:47]#[N:48].[K+]>CS(C)=O.O>[CH3:1][O:2][CH2:3][C@H:4]1[N:8]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:7][C@@H:6]([C:47]#[N:48])[CH2:5]1
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참가 물질

6

반응물 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 69514757trans-5-Methoxymethyl-3-tosyl-Cbz-pyrrolidine

생성물 1

HCID 60078795cis-5-Methoxymethyl-3-Cyano-Cbz-Pyrrolidine수율 69%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962
Water
용매

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온도
80 °C

실험 절차

5 (13.76 g, 0.034 mol) was dissolved in DMSO (17 mL). 18-Crown-6 (5 eq) and finely ground KCN (5 eq) were added and the reaction mixture was stirred for 6 h at 80° C. The reaction solution was diluted with H2O (17 mL) and then extracted with ethyl acetate. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (4/1, v/v) to afford 13.76 g (69% yield) of the desired product 6 as a colorless oil.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography
  5. washeluting with hexanes/ethyl acetate (4/1

출처 및 근거

ORD 기록
ord-387de7f4fa9a44198c1451ccf90ced71
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06710186B2

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