Hydrochloric Acid → HCID 178494572, compound

HRID 1900047Notes

Reaction equation

HRID 1900047 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5]1.[BH4-].[Na+].O.Cl>C(O)C.C(OCC)(=O)C.CCCCCC>[OH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([C:13]2[CH:12]=[CH:11][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:15][CH:14]=2)[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 23371853HCID 23371853, compound

Product 1

HCID 178494572HCID 178494572, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

5.0 g (16.44 mmol) of (RS)-5-methoxymethyl-3-[4-(4-oxo-cyclohexyl)-phenyl]-oxazolidin-2-one were dissolved in 150 ml of ethanol while heating and, after cooling, treated while stirring with 620 mg (16.4 mmol) of sodium borohydride, cooled overnight and the solvent was subsequently distilled off. The oily residue obtained was treated with water and 1N hydrochloric acid and the reaction product was taken up in ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and the solvent was distilled off. The colorless oil obtained (5.3 g) was dissolved in ethyl acetate, treated with hexane until turbid and the separated precipitate was filtered off under suction after 1 hour. 3.3 g of an alcohol which was uniform in the nmr spectrum were obtained. M.p. 109°-110°.

Workup

  1. temperaturewhile heating
  2. temperatureafter cooling
  3. additiontreated
  4. temperaturecooled overnight
  5. distillationthe solvent was subsequently distilled off
  6. customThe oily residue obtained
  7. washThe organic phase was washed with water
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe colorless oil obtained (5.3 g)
  11. filtrationthe separated precipitate was filtered off under suction after 1 hour
  12. customwere obtained

Sources & evidence

ORD record
ord-4135a24f5f294d05b10db43f5792b8fa
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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