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 473033Notes

Reaction equation

HRID 473033 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-70f84e2ed7d2464097416cf3b5addbfa
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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