Tetrabutylammonium Fluoride Trihydrate → 5-{(1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-8-(benzyloxy)quinolin-2(1H)-one

HRID 1925503Notes

Reaction equation

[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[C:39]5[C:34]=4[CH:35]=[CH:36][C:37](=[O:51])[NH:38]5)[O:25][Si](C(C)(C)C)(C)C)[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)=[C:39]5[C:34]=4[CH:35]=[CH:36][C:37](=[O:51])[NH:38]5)[OH:25])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of Intermediate 32 (0.48 g, 0.68 mmol) in tetrahydrofuran (12 mL) was added tetrabutylammonium fluoride trihydrate (0.284 g, 1.09 mmol). The reaction mixture was stirred at 45° C. for 3.5 hours. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed several times with water and the solvent was removed under reduced pressure to give the title compound as a yellow solid (0.375 g, 88%). MS (M+): 593.

Workup

customThe solvent was removed under reduced pressure
customthe crude was partitioned between ethyl acetate and water
washThe organic layer was washed several times with water
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-a23753e32f414c7b91506d663dbea864
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178679B2

Reaction notes

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