Tetrabutylammonium Fluoride → HCID 71533395, compound

HRID 1774792Notes

Reaction equation

C([SiH2][O:6][C:7](C)(C)[C@H:8]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]([CH3:29])[C:24](=[O:30])[CH2:23][CH2:22]3)[CH:16]=[N:17][CH:18]=1)[CH:9]([CH3:11])[CH3:10])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][CH2:7][C@H:8]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]([CH3:29])[C:24](=[O:30])[CH2:23][CH2:22]3)[CH:16]=[N:17][CH:18]=1)[CH:9]([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 10 mL round-bottomed flask, 6-{5-[(R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-propylamino]-pyridin-3-yl}-1-methyl-3,4-dihydro-1H-quinolin-2-one (60 mg, 132 μmol) was dissolved in THF (1.5 mL) to give a light yellow solution and cooled down to 0° C. TBAF, 1 M sol. in THF (132 μl, 132 μmol) was added dropwise. The solution was stirred at 0° C. for 1.5 h and partitioned between aqueous sat. NaHCO3 solution and AcOEt (3×). The organic layers were collected, dried over Na2SO4 and evaporated in vacuo. The crude material was purified by flash chromatography (silica gel, 20 g, 100% EtOAc followed by 1% MeOH in EtOAc) to give the title compound (22 mg, 49%) as a light yellow foam. MS: 340.2 (M+H+).

Workup

customto give a light yellow solution
custompartitioned between aqueous sat. NaHCO3 solution and AcOEt (3×)
customThe organic layers were collected
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 20 g, 100% EtOAc followed by 1% MeOH in EtOAc)

Sources & evidence

ORD record: ord-496333dd330a4a97a69f9e1a1800e475
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

Loading…