Decalin → HCID 67743311, compound

HRID 1900078Notes

Reaction equation

HRID 1900078 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])=[N:6][CH:7]=1.[CH3:14][O:15]CC1COC(=O)O1.[C:23](=O)([O-])[O-].[K+].[K+].C1C2C(CCCC2)CCC1>O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]([CH3:23])[CH:11]([O:15][CH3:14])[O:10][C:9]2=[O:13])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 7044DecalinHCID 11430Potassium CarbonateHCID 600000HCID 600000, compoundHCID 43844854-(Methoxymethyl)-1,3-dioxolan-2-one

Product 1

HCID 67743311HCID 67743311, compoundYield 308.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 9.3 g of ethyl 5-bromo-pyridin-2-yl-carbamate, 7.5 g of 4-methoxymethyl-1,3-dioxolan-2-one, 1.0 g of potassium carbonate and 10 ml of decahydronaphthalene was heated to 160° C. for 6 h. The mixture was cooled and treated with ethyl acetate and water. The phases were separated, the aqueous phase was extracted with ethyl acetate and the organic phase was washed with saturated sodium chloride solution. The organic phases were combined and dried with magnesium sulfate and then concentrated. Chromatography of the residue (20.2 g) with ethyl acetate/hexane mixtures (1:2-1:1) on silica gel yielded 6.4 g of (RS)-3-(5-bromo-pyridin-2-yl)-5-methoxy-methyl-oxazolidin-2-one which was recrystallized from diethyl ether. M.p.: 90°-92°.

Workup

  1. temperatureThe mixture was cooled
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washthe organic phase was washed with saturated sodium chloride solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a14eb7dfb9a245d1846f0fc581555f17
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

Loading…