N-bromobutanimide → tert-Butyl 2-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1848498Notes

Reaction equation

HRID 1848498 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][N:3]1[C:19]1[CH2:20][O:21][C:22](=[O:24])[CH:23]=1.[Br:25]N1C(=O)CCC1=O>C(Cl)Cl>[Br:25][C:23]1[C:22](=[O:24])[O:21][CH2:20][C:19]=1[N:3]1[CH2:4][CH2:5][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86709449Tert-butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 86709468tert-Butyl 2-(4-bromo-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-butyl 1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (I-16, Step A) (2.73 g, 8.12 mmol) was dissolved in DCM (70 mL) and was treated with N-bromosuccinimide (1.73 g, 9.74 mmol) at 25° C. and the resulting mixture was stirred overnight at room temperature. The next day, the reaction mixture was diluted with DCM and was washed with water and brine then dried over Na2SO4. Removing solvent gave crude product that was purified by silica gel column chromatography (80 g RediSep Gold Column) using (25-80) % EtOAc/Hexanes as mobile phase to afford the title compound.

Workup

  1. washwas washed with water and brine
  2. dry with materialthen dried over Na2SO4
  3. customRemoving solvent gave crude product that
  4. customwas purified by silica gel column chromatography (80 g RediSep Gold Column)

Sources & evidence

ORD record
ord-c98d1c5072f340a59a498bcbb286a265
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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