1,3-Dibromopropane → HCID 131722984, compound

HRID 429054Notes

Reaction equation

HRID 429054 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]1)[CH2:6][CH2:5]2.[Br:17][CH2:18][CH2:19][CH2:20]Br>[H-].[Na+].C(OCC)(=O)C>[Br:17][CH:18]([CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[C:7]21[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11]2)[CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 80011,3-DibromopropaneHCID 18354313HCID 18354313, compound

Product 1

HCID 131722984HCID 131722984, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24758Sodium hydrideSolvent

Conditions

Temperature
50 °C

Procedure

(+/−)-5′-fluoro-spiro[imidazolidine-4,1′indan]-2,5-dione (331 mg.,1.5 mmol) was dissolved in dry dimethylformaride (4 mL) and 60% sodium hydride in mineral oil (72 mg., 1.8 mmol) was added. The mixture was warmed at 50° C for 20 minutes and then 1,3-dibromo-propane (1.1 mL, 10.9 mmol) was added. The reaction mixture was warmed at 50° C. for 2 hours. The cooled reaction mixture was diluted with ethyl acetate and the organic solution was washed with aqueous Na2CO3 and water (3×). The dried extract was evaporated and chromatographed on silica gel using a 10-30% ethyl acetate/hexane gradient. The appropriate fractions were combined and evaporated to give the racemic product as a glassy solid which was used as is.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was warmed at 50° C. for 2 hours
  3. customThe cooled reaction mixture
  4. washthe organic solution was washed with aqueous Na2CO3 and water (3×)
  5. extractionThe dried extract
  6. customwas evaporated
  7. customchromatographed on silica gel using a 10-30% ethyl acetate/hexane gradient
  8. customevaporated

Sources & evidence

ORD record
ord-3b131cdecd3242948412d5043102951a
Source dataset
uspto-grants-2001_11
Patent number
US06316437B1

Reaction notes

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