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

HRID 473032Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[C:8]2=O)=[CH:4][CH:3]=1.[CH3:22][Si:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][S:26]([NH2:29])(=[O:28])=[O:27]>ClCCCl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]3)[C:8]2=[N:29][S:26]([CH2:25][CH2:24][Si:23]([CH3:31])([CH3:30])[CH3:22])(=[O:28])=[O:27])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of tert-butyl 6′-bromo-1′-oxo-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1-carboxylate (0.2863 g, 0.8 mmol), 2-(trimethylsilyl)ethanesulfonamide (0.2000 g, 1.1 mmol), and Ti(OEt)4 (0.6900 g, 3.0 mmol) in 1,2-dichloroethane (3 mL) was heated at 110° C. for 20 h. The reaction mixture was then quenched with ice, extracted with CH2Cl2, and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.4031 g (96%) of tert-butyl 6′-bromo-1′-(((2-(trimethylsilyl)ethyl)sulfonyl)imino)-1′,3′-dihydrospiro[azetidine-3,2′-indene]-1-carboxylate. LC-MS tR=2.31 min in 3 min chromatography, m/z 515, 517 (MH+), 459, 461 (MH+-56).

Workup

customThe reaction mixture was then quenched with ice
extractionextracted with CH2Cl2
dry with materialdried over Na2SO4
customAfter the solvent was evaporated under reduced pressure
customthe residue was purified by chromatography on silica gel
washeluted with hexanes/ethyl acetate

Sources & evidence

ORD record: ord-7e33ab24e5c54b29b38ab31f1b4f8be6
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633212B2

Reaction notes

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