Tetrabutylammonium Fluoride → (2S,4R)-methyl 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylate

HRID 1043432Notes

Reaction equation

HRID 1043432 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C@:21]1([C:39]2[CH:40]=[C:41]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([CH:51]=[CH2:52])[CH:46]=3)[CH:42]=[CH:43][CH:44]=2)[CH2:25][N:24](C(OCC[Si](C)(C)C)=O)[C@H:23]([C:35]([O:37][CH3:38])=[O:36])[CH2:22]1>C1COCC1.CCOC(C)=O>[CH3:19][O:20][C@:21]1([C:39]2[CH:40]=[C:41]([C:45]3[CH:50]=[CH:49][CH:48]=[C:47]([CH:51]=[CH2:52])[CH:46]=3)[CH:42]=[CH:43][CH:44]=2)[CH2:25][NH:24][C@H:23]([C:35]([O:37][CH3:38])=[O:36])[CH2:22]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59266553(2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 59266492(2S,4R)-methyl 4-methoxy-4-(3'-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylateYield 108.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBAF (1.0M in THF, 19 mL, 19 mmol) was added to a solution of (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-methoxy-4-(3′-vinylbiphenyl-3-yl)pyrrolidine-1,2-dicarboxylate (2.3 g, 4.78 mmol) in THF (30 mL) and stirred at r.t. overnight. The reaction was diluted with EtOAc and washed with water and then brine. The organic layer was collected, dried over MgSO4, filtered and evaporated to give (2S,4R)-methyl 4-methoxy-4-(3′-vinylbiphenyl-3-yl)pyrrolidine-2-carboxylate (1.75 g, 5.19 mmol, 100% yield) as a yellow oil. LCMS: rt=1.42 min. [M-OMe]+=306; 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 uL; wavelength=220.

Workup

  1. washwashed with water
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f6bf45b2f71e41e0b9cb92c39907165d
Source dataset
uspto-grants-2013_10
Patent number
US08563505B2

Reaction notes

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