Butyl bromide → HCID 14836223, compound

HRID 1087761Notes

Reaction equation

HRID 1087761 reaction equation
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH3:20]>C1COCC1.CN(C=O)C>[CH2:17]([N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 5596684-Benzyl-1,3-oxazolidin-2-one

Product 1

HCID 14836223HCID 14836223, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of 5.005 g of 2-amino-3-phenylpropanol and 3 g of ethylene carbonate in 50 ml of toluene in a round bottom flask with a Dean-Stark trap was refluxed for 48 hours and the reaction was followed by tlc. At the end of the reaction the solution was washed with water and brine and concentrated to dryness to give 5.86 g of light yellow oil. The racemic 4-benzyloxazolidin- 2-one was dissolved in 20 ml of THF and was added to 1.98 g of 60% NaH in 40 ml of THF and 10 ml of DMF. After the initial reaction had subsided the reaction mixture was refluxed for 2 hours. After cooling to r.t. 5.44 g of 1-bromobutane in 20 ml of THF was added and the reaction mixture was refluxed overnight. It was then poured into ice-water and extracted twice with ethyl acetate. Combined organic extracts were washed three times with water, followed by brine. After drying, the solution was concentrated to give 7.625 g of crude oil. This was kugelrohr distilled (155°-160° C./0.3 mm) to give 6.54 g (84.7% overall yield) of product.

Workup

  1. customAfter the initial reaction
  2. temperaturewas refluxed for 2 hours
  3. temperaturethe reaction mixture was refluxed overnight
  4. extractionextracted twice with ethyl acetate
  5. washCombined organic extracts were washed three times with water
  6. customAfter drying
  7. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-9d0eaec2654e40d291de05459c37abdb
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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