1-Bromo-4-(1,4-dibromobutyl)benzene → (5R*,6S*)-6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester

HRID 489233

Reaction equation

HRID 489233 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](Br)[CH2:9][CH2:10][CH2:11]Br)=[CH:4][CH:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:25][C:24](=[O:26])[N:23]([C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=2)[C:22]1=[O:35])=[O:20])([CH3:17])([CH3:16])[CH3:15]>>[C:14]([O:18][C:19]([N:21]1[C@@:25]2([CH2:11][CH2:10][CH2:9][C@H:8]2[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[C:24](=[O:26])[N:23]([C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=2)[C:22]1=[O:35])=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

3

Reactant 2

HCID 220252951-Bromo-4-(1,4-dibromobutyl)benzeneHCID 235885583-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 60054799(5R*,6S*)-6-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-diazaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester

Procedure

Using the same procedure as in Example 1 starting from 1-bromo-4-(1,4-dibromobutyl)benzene (153 mg, 0.4 mmol) (Preparation 4) and 3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxylic acid tert-butyl ester (113 mg, 0.33 mmol) (Preparation 11), the above-titled compound was obtained (33 mg) as a white solid. 1H NMR (CDCl3): 7.48 (2H, d, J=8.3 Hz), 7.30 (1H, m), 7.07 (2H, d, J=8.3 Hz ), 6.52 (2H, m), 4.06 (1H, dd, J1=13.1 Hz, J2=5.5 Hz), 2.35-2.6 (3H, m), 2-2.35 (3H, m), 1.66 (9H, s).

Sources & evidence

ORD record
ord-1a254deca7ae44f3bcdfb55ed14b0459
Source dataset
uspto-grants-2005_12
Patent number
US06977267B2

Linked notes

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