Ethanol → HCID 23371889, compound

HRID 1900048Notes

Reaction equation

HRID 1900048 reaction equation
C(O[CH:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:10]1)C1C=CC=CC=1.[CH2:28]([OH:30])C>[Pd]>[OH:30][CH2:28][CH:9]1[O:13][C:12](=[O:14])[N:11]([C:15]2[CH:16]=[CH:17][C:18]([CH:21]3[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]3)=[CH:19][CH:20]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 702EthanolHCID 23371879HCID 23371879, compound

Product 1

HCID 23371889HCID 23371889, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4.9 g (12.9 mmol) of (RS)-5-benzyloxy-3-[4-(4-oxo-cyclohexyl)-phenyl]-oxazolidin-2-one were dissolved in 500 ml of ethanol while heating and, after adding 5% Pd/C, hydrogenated at room temperature. After separating the catalyst the solvent was distilled off and the oil obtained was chromatographed on a 30-fold amount of silica gel. The methylene chloride-ethyl acetate (1:4) eluates were pooled and the solvent was distilled off. 3.2 g of product were obtained from ethyl acetate/hexane. M.p.: 151.5°-152.5°.

Workup

  1. temperaturewhile heating
  2. customhydrogenated at room temperature
  3. customAfter separating the catalyst the solvent
  4. distillationwas distilled off
  5. customthe oil obtained
  6. customwas chromatographed on a 30-fold amount of silica gel
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8cb473486ad44c9fa50e4cce3cb152ad
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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