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 1503456Notes

Reaction equation

HRID 1503456 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

4

Reactant 2

HCID 110085532-(Trimethylsilyl)ethane-1-sulfonamideHCID 581983161-Boc-6'-bromo-1'-oxo-1',3'-dihydrospiro[azetidine-3,2'-indene]

Product 1

HCID 67043711Tert-butyl 6'-bromo-1'-(((2-(trimethylsilyl)ethyl)sulfonyl)imino)-1',3'-dihydrospiro[azetidine-3,2'-indene]-1-carboxylateYield 97.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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

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

Sources & evidence

ORD record
ord-438d5c83091a457c91467a3af94fc8a7
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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