Sodium hydride → 1,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione

HRID 53898노트

반응식

HRID 53898 반응식
[NH:1]1[C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22][N:1]1[C:5]2[C:6](=[O:12])[N:7]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1)([CH3:18])[CH3:17]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 3085877Aldisine

생성물 1

HCID 110589801,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione수율 48%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A 500 mg amount of the 6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione (aldisin) described in the reference (Prager, R. et al: Aust. J. Chem., 43, p. 355-365 (1990)) was added to a 20 ml dimethylformamide suspension of 252 mg of sodium hydride (60% oil). The mixture was stirred at room temperature for 1 hour. A 1.12 ml amount of trimethylsilylethoxymethyl chloride was added under ice cooling, the mixture was stirred at room temperature for 3 hours, then a saturated aqueous solution of ammonium chloride was added and extraction was performed by ethyl acetate. The extract was washed with saturated saline, dried, filtered, and concentrated under reduced pressure to obtain a residue which was purified by silica gel column chromatography (hexane:ether acetate=6:1) to obtain 623 mg of the above-referenced compound (8) (yield 48%).

후처리

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextraction
  3. washThe extract was washed with saturated saline
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue which
  8. customwas purified by silica gel column chromatography (hexane:ether acetate=6:1)

출처 및 근거

ORD 기록
ord-1c18622ef01b47798c68d59f65e97b4b
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05621099

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