Tert-butyl 6'-bromo-1'-(((2-(trimethylsilyl)ethyl)sulfonyl)imino)-1',3'-dihydrospiro[azetidine-3,2'-indene]-1-carboxylate → Tert-butyl 6'-bromo-1'-(2-(trimethylsilyl)ethylsulfonamido)-1'-vinyl-1',3'-dihydrospiro[azetidine-3,2'-indene]-1-carboxylate

HRID 1503457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1503457
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21]3)[C:8]2=[N:11][S:12]([CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:4][CH:3]=1.[CH:31]([Mg]Br)=[CH2:32]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:21][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23]3)[C:8]2([NH:11][S:12]([CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])(=[O:14])=[O:13])[CH:31]=[CH2:32])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 67043711Tert-butyl 6'-bromo-1'-(((2-(trimethylsilyl)ethyl)sulfonyl)imino)-1',3'-dihydrospiro[azetidine-3,2'-indene]-1-carboxylateHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 67043873Tert-butyl 6'-bromo-1'-(2-(trimethylsilyl)ethylsulfonamido)-1'-vinyl-1',3'-dihydrospiro[azetidine-3,2'-indene]-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 6′-bromo-1′-(((2-(trimethylsilyl)ethyl)sulfonyl)imino)-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1-carboxylate (0.4031 g, 0.78 mmol) in THF (3 mL) was added vinylmagnesium bromide (1.0 M in THF, 3 mL, 3.0 mmol) at 0° C. under nitrogen. The mixture was allowed to slowly warm to room temperature over 18 h. The reaction mixture was then quenched with saturated NH4Cl, extracted with EtOAc, and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the crude product was directly used in the next step without further purification. LC-MS tR=2.31 min in 3 min chromatography, m/z 543, 545 (MH), 487, 489 (MH+-56).

Aufarbeitung

  1. customThe reaction mixture was then quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe crude product was directly used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-05609566eb194c499fd94357acf0935c
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212153B2

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