Tetrabutylammonium Fluoride → (2S,4R)-methyl 4-(4'-(dimethylamino)-2'-vinylbiphenyl-4-yl)-4-methoxypyrrolidine-2-carboxylate
Reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][N:20]([CH3:55])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C@@:33]3([O:51][CH3:52])[CH2:37][N:36](C(OCC[Si](C)(C)C)=O)[C@H:35]([C:47]([O:49][CH3:50])=[O:48])[CH2:34]3)=[CH:29][CH:28]=2)=[C:23]([CH:53]=[CH2:54])[CH:22]=1>C1COCC1>[CH3:55][N:20]([CH3:19])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][C:30]([C@@:33]3([O:51][CH3:52])[CH2:37][NH:36][C@H:35]([C:47]([O:49][CH3:50])=[O:48])[CH2:34]3)=[CH:31][CH:32]=2)=[C:23]([CH:53]=[CH2:54])[CH:22]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
TBAF (1.0M in THF, 1.7 mL, 1.7 mmol) was added to a solution of (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-(4′-(dimethylamino)-2′-vinylbiphenyl-4-yl)-4-methoxypyrrolidine-1,2-dicarboxylate (231 mg, 0.440 mmol) in THF (5 mL) and stirred at r.t. for 1 hr. The reaction was evaporated to give crude (2S,4R)-methyl 4-(4′-(dimethylamino)-2′-vinylbiphenyl-4-yl)-4-methoxypyrrolidine-2-carboxylate (167 mg, 0.439 mmol, 100% yield) as an orange oil used directly in next steps with no purification. LCMS: rt=1.01 min. [M-OMe]+=349; Phenomenex-Luna C-18 (5μ) (3.0×50 mm); Solvent A=10% acetonitrile—90% water—0.1% TFA, Solvent B=90% acetonitrile—10% water—0.1% TFA; gradient 0% to 100% solvent B over 2 min. and then hold for 1 min.; 4 mL/min; inj. vol.=5 μL; wavelength=220.
Workup
- customThe reaction was evaporated
Sources & evidence
- ORD record
- ord-3acb515a2b954f68ae407b9d69186fae
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563505B2
Reaction notes
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