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

HRID 1366574Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-3774748bdb24401f94a189838d9348ac
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

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