Hydrochloric Acid → HCID 131719242, compound

HRID 374894Notes

Reaction equation

HRID 374894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:28])[CH2:15]C3CCC4OCC(=O)CC=4OC3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+].[OH2:31].Cl.[CH3:33][OH:34]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:28])[CH2:15][CH:9]3[O:34][C:33]4[CH2:5][CH2:6][CH2:7][CH2:2][O:31][C:3]=4[CH:4]=[C:8]3[OH:12])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 189963407-(2-(5-(3-Chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,5-dioxabenzocycloheptan-3-one

Product 1

HCID 131719242HCID 131719242, compound

Procedure

One equivalent of 5-(3-chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone, prepared by the procedure of U.S. Pat. No. 5,061,727 Example 1, is treated with one equivalent of 1,3-dibromoacetone and excess potassium carbonate in acetonitrile. The mixture is stirred at room temperature for 18 hours, filtered and evaporated in vacuo to give 7-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl)-1,5-dioxabenzocycloheptan-3-one. One equivalent of this ketone is reduced, at room temperature for one hour, with excess sodium borohydride in methyl alcohol. The reaction mixture is poured into water, made acidic with 1N hydrochloric acid and extracted with methylene chloride. The organic extracts are dried and evaporated in vacuo to give 7-(2-(5-(3-chlorophenyl)-2-oxo-3-oxazolidinyl)propyl-1,5-dioxabenzocycloheptan-3-ol. Hydrolysis with 2.5N sodium hydroxide gives the title compound.

Workup

  1. extractionextracted with methylene chloride
  2. customThe organic extracts are dried
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-12b1efd400d64ec79bd3db4ca9efa5c8
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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