1-(Triphenylphosphoranylidene)acetone → 1-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one

HRID 440096노트

반응식

HRID 440096 반응식
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:25][C:26](=[O:28])[CH3:27])C=CC=CC=1>C1C=CC=CC=1>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][CH:12]1[CH:13]=[CH:25][C:26](=[O:28])[CH3:27])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

참가 물질

4

반응물 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 572702461-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one수율 69%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

To a stirred solution of N-Cbz-L-prolinal (6.3 g, 27 mmol, from step 24d above) in 30 mL of benzene was added 9.42 g (29.6 mmol) of 1-triphenylphosphoranylidene-2-propanone (Aldrich) at room temperature. The reaction mixture was heated to reflux for 4 hr. The benzene was removed under vacuum, and the residue was dissolved in ether and cooled for 16 hr. The phosphine oxide by product was removed by filtration, and the solution was further purified by column chromatography on silica gel, eluting with 20% ethyl acetate in hexanes, to afford 4.4 g of the title product (69% yield).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hr
  3. customThe benzene was removed under vacuum
  4. dissolutionthe residue was dissolved in ether
  5. temperaturecooled for 16 hr
  6. customThe phosphine oxide by product was removed by filtration
  7. customthe solution was further purified by column chromatography on silica gel
  8. washeluting with 20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-fd7d853d1ad9403c8c3b1b2c8e4ceed7
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516912

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