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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
ノート
印刷プレビュー

反応式

HRID 1043417 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒

2
HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-69401695749b4dc888495a057dc6487c
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08563505B2

反応ノート

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