Water → (5R*,6S*)-6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione

HRID 489230

Reaction equation

HRID 489230 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10](Br)[CH2:11][CH2:12][CH2:13]Br)=[CH:6][CH:5]=1.[Cl:16][C:17]1[CH:18]=[C:19]([N:24]2[C:28](=[O:29])[CH2:27][N:26]([CH3:30])[C:25]2=[O:31])[CH:20]=[C:21]([Cl:23])[CH:22]=1.O>CS(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:11][CH2:12][CH2:13][C@:27]32[N:26]([CH3:30])[C:25](=[O:31])[N:24]([C:19]2[CH:18]=[C:17]([Cl:16])[CH:22]=[C:21]([Cl:23])[CH:20]=2)[C:28]3=[O:29])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 119945103-(3,5-Dichlorophenyl)-1-methylimidazolidine-2,4-dioneHCID 220252951-Bromo-4-(1,4-dibromobutyl)benzene

Product 1

HCID 60054691(5R*,6S*)-6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dioneYield 110.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

KOH flakes (1.3 g, 23.2 mmol) were added at RT to a solution of 1-bromo-4-(1,4-dibromobutyl)benzene (4.08 g, 10.6 mmol) (Preparation 4) and 3-(3,5-dichlorophenyl)-1-methylimidazolidine-2,4-dione (2.5 g, 9.6 mmol, prepared according to Fujinami et al. cited above) in dry DMSO (40 ml). After 30 h at RT, the reaction mixture was poured into water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to yield an orange oil (4.98 g) which was chromatographed over silica gel (DCM/pentane 50/50) to give 6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (2.1 g) as a white solid having the relative stereochemistry depicted above. 1H NMR (CDCl3): 7.45 (2H, d, J=8.4 Hz), 7.25 (1H, m), 7.03 (2H, d, J=8.4 Hz), 6.65 (2H, m), 3.36 (1H, dd, J1=12.9 Hz, J2=6.2 Hz), 3.13 (3H, s), 2.4-2.65 (1H, m), 1.8-2.4 (5H, m).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c749bfdba65b4784a70ccf2716bed8cc
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Linked notes

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