Tetrabutylammonium Fluoride → HCID 58464054, compound

HRID 1894223Notes

Reaction equation

C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][N:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][N:15]=2)[C:8]1=[O:28])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH:7]1[C:11]([CH3:13])([CH3:12])[CH2:10][N:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:16][N:15]=2)[C:8]1=[O:28]

Participants

Conditions

Temperature: 60 °C

Procedure

(100 mg, 0.18 mmol) (3RS)-3-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-1-(5-phenylethynyl-pyridin-2-yl)-pyrrolidin-2-one (Example 14, step 6) was dissolved in THF (1 ml) and TBAF (1M in THF) (184 μl, 0.184) was added drop wise at room temperature. The mixture was stirred for 1 hr at 60° C. The reaction mixture was extracted with sat. NaHCO3-solution and two times EtOAc. The organic layers were extracted with water, dried over Na2SO4, filtered and evaporated to dryness. The crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired (3RS)-3-hydroxy-4,4-dimethyl-1-(5-phenylethynyl-pyridin-2-yl)-pyrrolidin-2-one (44 mg, 78% yield) was obtained as a white solid, MS: m/e=307.3 (M+H+).

Workup

extractionThe reaction mixture was extracted with sat. NaHCO3-solution and two times EtOAc
extractionThe organic layers were extracted with water
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated to dryness
customThe crude material was purified by flash chromatography on silica gel (20 gr, ethyl acetate/heptane gradient, 0:100 to 100:0)

Sources & evidence

ORD record: ord-687342f0299642d5b108a076bfac2279
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513273B2

Reaction notes

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