tert-butyl 1-(methoxy(methyl)carbamoyl)-3-phenyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxylate → tert-butyl 1-(3,3-dimethylbutanoyl)-3-phenyl-5,6-dihydro-imidazo[1,5-a]pyrazine-7(8H)-carboxylate

HRID 1971106Notes

Reaction equation

CON(C)[C:4]([C:6]1[N:7]=[C:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C:10]=12)=[O:5].[CH2:29]([Mg]Cl)[C:30]([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[CH3:29][C:30]([CH3:33])([CH3:32])[CH2:31][C:4]([C:6]1[N:7]=[C:8]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:11][C:10]=12)=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound 26A (0.10 g, 0.26 mmol) was dissolved in THF and cooled to 0° C. and neopentylmagnesium chloride (1M in diethyl ether, 0.35 mL) was added and the mixture was stirred for 2 hours. The mixture was quenched with NH4Cl saturated solution and extracted with EtOAc. The residue was purified by preparative flash chromatography on silica, eluting with 20-80% gradient of ethyl acetate in hexanes to provide intermediate 26B (0.08 g, 77%).

Workup

customThe mixture was quenched with NH4Cl saturated solution
extractionextracted with EtOAc
customThe residue was purified by preparative flash chromatography on silica
washeluting with 20-80% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record: ord-93b3b4c01d1943bc969973e5dff8bf66
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431565B2

Reaction notes

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