Benzyl Bromide → 4-Methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane-5,8-dione

HRID 1366574노트

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HRID 1366574 반응식
[H-].[Na+].[CH3:3][N:4]1[C:11](=[O:12])[CH2:10][NH:9][C:8](=[O:13])[C:5]21[CH2:7][CH2:6]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C.O>[CH3:3][N:4]1[C:11](=[O:12])[CH2:10][N:9]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8](=[O:13])[C:5]21[CH2:7][CH2:6]2

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 669363934-Methyl-4,7-diazaspiro[2.5]octane-5,8-dione

생성물 1

HCID 669362214-Methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane-5,8-dione수율 54.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

Sodium hydride (302 mg, 12.62 mmol) was taken up in DMF (10 mL) and cooled to 0° C. for 30 min. Then a mixture 4-methyl-4,7-diazaspiro[2.5]octane-5,8-dione (1.769 g, 11.47 mmol) in DMF (5 mL) was slowly added over 10 min. This mixture was allowed to stir for 45 min, and then benzyl bromide (4.08 mL, 34.41 mmol) was added, and the reaction was stirred for 45 min further. The mixture was carefully diluted with water (10 mL) and concentrated in vacuo. The resulting crude product was purified via reverse phase HPLC to provide 4-methyl-7-(phenylmethyl)-4,7-diazaspiro[2.5]octane-5,8-dione (1.535 g, 54%). LCMS: (M+H)+: 245.1.

후처리

  1. stirringthe reaction was stirred for 45 min further
  2. concentrationconcentrated in vacuo
  3. customThe resulting crude product was purified via reverse phase HPLC

출처 및 근거

ORD 기록
ord-3774748bdb24401f94a189838d9348ac
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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