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

HRID 1043432노트

반응식

HRID 1043432 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f6bf45b2f71e41e0b9cb92c39907165d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563505B2

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