Methyl iodide → 1-benzyloxycarbonyl-3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]Pyrrolidine

HRID 600897노트

반응식

HRID 600897 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@@H:13]([C:16]2([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27]I>[Ag]=O.CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@@H:13]([C:16]2([N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:27])[CH2:18][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 6328Methyl iodideHCID 11132144(3R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)pyrrolidine

생성물 1

HCID 229403761-benzyloxycarbonyl-3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]Pyrrolidine수율 89.9%

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

1-benzyloxycarbonyl-3-(R)-[1-(tert-butoxycarbonylamino)cyclopropyl]pyrrolidine (1.40 g, 3.89 mmol), N,N′-dimethylformamide (7 ml), silver oxide (9.0 g, 39 mmol) and methyl iodide (24 ml, 389 mmol) were placed in a shaded and sealed tube, and this mixture was stirred for 13 hours in an oil bath of 80° C. The reaction solution was then filtered through cellite (ethyl acetate washing) and the filtrate was then diluted with ethyl acetate (100 ml). The organic layer was then washed with water (50 ml×3) and saturated saline solution (50 ml) in that order, and dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the concentrate was applied to a silica gel chromatography, and 1.31 g (89%) of the title compound was obtained in the form of a pale-yellow syrup an n-hexane:ethyl acetate=2:1 eluate. The instrumental analysis data for this resulting compound agreed with the data indicated in PCT/JP96/00208.

후처리

  1. customsealed tube
  2. filtrationThe reaction solution was then filtered through cellite (ethyl acetate washing)
  3. additionthe filtrate was then diluted with ethyl acetate (100 ml)
  4. washThe organic layer was then washed with water (50 ml×3) and saturated saline solution (50 ml) in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtering
  7. concentrationthe filtrate was concentrated under a reduced pressure

출처 및 근거

ORD 기록
ord-5ce6f1ce1a34463fa179b1935fa51144
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902226B2

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