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Magnesium → (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-hydroxy-4-(2-vinylbiphenyl-4-yl)pyrrolidine-1,2-dicarboxylate

HRID 1043417
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HRID 1043417 반응식
[CH:1]([C:3]1[CH:8]=[C:7]([Mg]Br)[CH:6]=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH2:2].BrC1C=CC(C2C=CC=CC=2)=C(C=C)C=1.[Mg].[O:33]=[C:34]1[CH2:38][N:37]([C:39]([O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])=[O:40])[C@H:36]([C:48]([O:50][CH3:51])=[O:49])[CH2:35]1>C1COCC1.C1(C)C=CC=CC=1>[OH:33][C@:34]1([C:7]2[CH:6]=[CH:5][C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:3]([CH:1]=[CH2:2])[CH:8]=2)[CH2:38][N:37]([C:39]([O:41][CH2:42][CH2:43][Si:44]([CH3:46])([CH3:47])[CH3:45])=[O:40])[C@H:36]([C:48]([O:50][CH3:51])=[O:49])[CH2:35]1
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참가 물질

7

반응물 4

HCID 5462224MagnesiumHCID 59266363(S)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-oxopyrrolidine-1,2-dicarboxylateHCID 592665654-Bromo-2-vinylbiphenylHCID 178436727HCID 178436727, 화합물

생성물 1

HCID 59266520(2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-hydroxy-4-(2-vinylbiphenyl-4-yl)pyrrolidine-1,2-dicarboxylate수율 18.2%

시약·촉매·용매

2
HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

(2-vinylbiphenyl-4-yl)magnesium bromide (2.66 g, 9.38 mmol) solution, made by refluxing Intermediate 7 with 1 eq. of magnesium turnings in THF, was added to a solution of (S)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-oxopyrrolidine-1,2-dicarboxylate (2.7 g, 9.38 mmol) in toluene (75 mL) at 0° C. and stirred for 1 hr and then quenched with sat. NH4Cl solution. The aqueous layer was extracted with DCM and the combined organics were dried, filtered and evaporated to give crude material. The crude material was purified by flash chromatography on the Biotage (20-33% EtOAc:Hex) to give (2S,4R)-2-methyl 1-(2-(trimethylsilyl)ethyl) 4-hydroxy-4-(2-vinylbiphenyl-4-yl)pyrrolidine-1,2-dicarboxylate (800 mg, 1.711 mmol, 18% yield). LCMS: rt=1.85 min. [M+Na]+=490; 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. customquenched with sat. NH4Cl solution
  2. extractionThe aqueous layer was extracted with DCM
  3. customthe combined organics were dried
  4. filtrationfiltered
  5. customevaporated
  6. customto give crude material
  7. customThe crude material was purified by flash chromatography on the Biotage (20-33% EtOAc:Hex)

출처 및 근거

ORD 기록
ord-69401695749b4dc888495a057dc6487c
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563505B2

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