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

HRID 600897ノート

反応式

HRID 600897 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5ce6f1ce1a34463fa179b1935fa51144
出典データセット
uspto-grants-2011_03
特許番号
US07902226B2

反応ノート

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