Tetrahydrofuran → 1-(N-benzyloxy-N-methylcarbamoyl)-3-(3,5-di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one

HRID 1109293Notes

Reaction equation

[C:1]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[CH:8]=[C:9]1[CH2:13][CH2:12][NH:11][C:10]1=[O:14])([CH3:4])([CH3:3])[CH3:2].[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C(OCC)(=O)C>[CH2:25]([O:26][N:11]([CH3:12])[C:10]([N:11]1[CH2:12][CH2:13][C:9](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:17]([OH:18])=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:15]=2)[C:10]1=[O:14])=[O:14])[C:24]1[CH:23]=[CH:27][CH:3]=[CH:1][CH:2]=1

Participants

Conditions

Temperature: -70 °C

Procedure

3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)pyrrolidin-2-one (3.01 g, 10 mmole) was dissolved into THF (60 ml), which was cooled to -70° C. To this mixture, a solution of 1.0M lithium bis(trimethylsilyl)amide dissolved into THF (24 ml) was added. Furthermore, N-benzyloxy-N-methylphenylcarbamate (2.9 g, 12 mmole) was added thereto and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ethyl acetate, which was washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was separated by using silica gel chromatography (toluene:ethyl acetate=10:1), whereby 1.5 g of the objective compound (Ia-11) was obtained as white amorphous in 32% yield.

Workup

additionwas added
washwas washed with an aqueous solution of 0.1N hydrochloric acid, water, and saturated brine
dry with materialdried over magnesium sulfate
customevaporated
customThe obtained residue was separated

Sources & evidence

ORD record: ord-5f30ff28abce48cdb8f2d957a23ed1e8
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05319100

Reaction notes

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