2-Bromopropane → HCID 178458486, compound

HRID 2235243Notes

Reaction equation

HRID 2235243 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([OH:26])=[CH:21][C:20]=3[Cl:27])[C:14]2=[O:28])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].Br[CH:32]([CH3:34])[CH3:33].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[C:20]([Cl:27])=[CH:21][C:22]([O:26][CH:32]([CH3:34])[CH3:33])=[CH:23][C:24]=3[Cl:25])[C:14]2=[O:28])[CH2:9][CH2:8]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178455342HCID 178455342, compound

Product 1

HCID 178458486HCID 178458486, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add 1-[cis-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-one (Preparation 72) (0.543 g, 1.15 mmol), 2-bromopropane (0.212 g, 1.72 mmol), and potassium carbonate (0.365 g, 2.64 mmol) together with acetone (10 mL) and reflux overnight. Concentrate the reaction mixture under reduced pressure to give a residue. Purify the residue over silica gel, (98:2 dichloromethane in methanol) to give 0.080 g (14%) of the title compound: mass spectrum m/z: 516(M+1).

Workup

  1. temperaturereflux overnight
  2. concentrationConcentrate the reaction mixture under reduced pressure
  3. customto give a residue
  4. customPurify the residue over silica gel, (98:2 dichloromethane in methanol)

Sources & evidence

ORD record
ord-7d86a058ab8047aaae9f71849b85d7bc
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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