Lithium Hexamethyldisilazide → Methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-((triisopropylsilyloxy) methyl)phenyl)propanoate

HRID 1020093Notes

Reaction equation

[Li+].[CH3:2][Si]([N-][Si](C)(C)C)(C)C.[CH:11]([Si:14]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1)([CH3:13])[CH3:12].Br[C:35]1[C:36](C)=[C:37]2[C:42](=[O:43])[NH:41][C:39](=[O:40])[C:38]2=[CH:44][CH:45]=1>C1COCC1>[O:43]=[C:42]1[C:37]2[C:38](=[CH:44][CH:45]=[CH:35][CH:36]=2)[C:39](=[O:40])[N:41]1[CH2:2][CH:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:15][Si:14]([CH:11]([CH3:12])[CH3:13])([CH:28]([CH3:30])[CH3:29])[CH:31]([CH3:33])[CH3:32])=[CH:18][CH:19]=1)[C:24]([O:26][CH3:27])=[O:25]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of LiHMDS in THF cooled to −78° C. was added a cooled solution (−78° C.) of methyl 2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate (E133) in THF via syringe. The solution was stirred at −78° C. for 30 min. Bromo-methyl phthalimide was added directly to the anion and the solution stirred for 2 h at −78° C. The reaction was then poured into NH4Cl(sat) and extracted with EtOAc. The organics were dried (MgSO4), filtered, and evaporated. Column chromatography (SiO2, 0-20% EtOAc/Hexanes) gave pure methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoate (E134).

Workup

stirringthe solution stirred for 2 h at −78° C
extractionextracted with EtOAc
dry with materialThe organics were dried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-42b907b160c24eae8c0dba66ef3448a9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716310B2

Reaction notes

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