Potassium Bromide → 2-(4-Isopropoxy-phenyl)-2-aza-spiro[4.5]decane-1,8-dione

HRID 2368806Notes

Reaction equation

HRID 2368806 reaction equation
[OH:1][CH:2]1[CH2:22][CH2:21][C:5]2([C:9](=[O:10])[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH:18]([CH3:20])[CH3:19])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].C(=O)(O)[O-].[Na+]>ClCCl.O.Cl[O-].[Na+]>[CH:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:7][CH2:6][C:5]3([CH2:21][CH2:22][C:2](=[O:1])[CH2:3][CH2:4]3)[C:9]2=[O:10])=[CH:12][CH:13]=1)([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 58230130HCID 58230130, compound

Product 1

HCID 582300492-(4-Isopropoxy-phenyl)-2-aza-spiro[4.5]decane-1,8-dioneYield 71.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 23665760Sodium HypochloriteSolvent

Procedure

To a solution of 8-hydroxy-2-(4-isopropoxy-phenyl)-2-aza-spiro[4.5]decan-1-one (7 g) and 2,2,6,6-tetramethylpiperidine-1-oxyl (721 mg) in dichloromethane (250 ml) were added sequentially a solution of potassium bromide (549 mg) in water (60 ml), sodium hypochlorite (52.8 ml), sodium bicarbonate (5.81 g) and the reaction mixture was then stirred for 3 hour at RT. The reaction mixture was poured into ice/water and extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated off. The residue was purified by flash chromatography (silica gel, gradient 0% to 50% ethyl acetate in heptane) to give the title compound as a brown solid (5 g). MS (m/e): 302.174 [MH+].

Workup

  1. extractionextracted three times with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated off
  6. customThe residue was purified by flash chromatography (silica gel, gradient 0% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6cfad00cd7be4ff892de14b08e4542eb
Source dataset
uspto-grants-2014_04
Patent number
US08703807B2

Reaction notes

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