Benzyl Bromide → HCID 86692160, compound

HRID 2201752Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16]2.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:30]([CH:16]1[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([O:12][CH3:11])[CH:14]=2)[C:18](=[O:22])[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium bis(trimethysilyl)amide (4.8 mL, 4.8 mmol, 1 M in THF) was added to a solution of the tert-butyl 5-methoxy-1-oxoisoindoline-2-carboxylate (0.975 g) in THF (7 mL) at −78° C. After stirring the solution at −78° C. for 1 hr, benzyl bromide (0.88 mL, 7.41 mmol) was added, this was stirred at −78° C. for 1.5 hours. LC/MS showed complete conversion. Quenched the reaction mixture with saturated NaCl solution, then extracted with ethyl acetate, the combined organic layer was washed 1× with saturated NaCl solution. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 25-40% ethyl acetate in hexane, 0.92 g (2.59 mmol, 70%) of the product was obtained.

Workup

stirringthis was stirred at −78° C. for 1.5 hours
customQuenched the reaction mixture with saturated NaCl solution
extractionextracted with ethyl acetate
washthe combined organic layer was washed 1× with saturated NaCl solution
customThe organic phase was dried on Na2SO4
customthe solvent was evaporated
customThe residue was purified by flash-chromatography on silica gel with 25-40% ethyl acetate in hexane

Sources & evidence

ORD record: ord-b3a65a8ef0ba4d0fb6ff4f2c1770c9d4
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365512B2

Reaction notes

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