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

HRID 1792865ノート

反応式

HRID 1792865 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-505d61d455ad42dea1fa0ca92d5dd593
出典データセット
uspto-grants-2006_07
特許番号
US07078420B2

反応ノート

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