Hydrochloric Acid → (4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

HRID 1600355Notes

Reaction equation

HRID 1600355 reaction equation
[CH2:1]([C@H:8]1[C@@H:12]([C:13](O)=[O:14])[O:11][C:10](=[O:16])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[BH4-].[Na+].Cl>C(O)C.O>[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][OH:14])[O:11][C:10](=[O:16])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4311764Sodium borohydrideHCID 14558093(4S,5S)-2-Oxo-4-(phenylmethyl)-5-oxazolidinecarboxylic acid

Product 1

HCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

22.1 g (100 mmol) of (4S,5S)-4-benzyl-oxazolidin-2-one-5-carboxylic acid were dissolved in 120 ml of ethanol. 1.2 ml of concentrated sulphuric acid(11 mmol) were added and the mixture refluxed for 2 hours. 90 ml of ethanolwere then removed by distillation. This solution was then added dropwise within 30 minutes to a suspension of 5.3 g (140 mmol) of NaBH4 in 40 ml of ethanol. Once addition was complete, stirring was continued for 3 hours. 100 ml of water were cautiously added to the colourless suspension and a pH value of 7 was established with concentrated HCl. After 2 hours' stirring at room temperature, the temperature was reduced to 0° C. for a further 2 hours. The solid was filtered out and washed with a littleiced water. The product was then dried under a vacuum at 45° C.

Workup

  1. temperaturethe mixture refluxed for 2 hours
  2. custom90 ml of ethanolwere then removed by distillation
  3. additionOnce addition
  4. stirringAfter 2 hours' stirring at room temperature
  5. waitthe temperature was reduced to 0° C. for a further 2 hours
  6. filtrationThe solid was filtered out
  7. washwashed with a littleiced water
  8. customThe product was then dried under a vacuum at 45° C.

Sources & evidence

ORD record
ord-8ed49918bd134a54b6f95c471b485ed8
Source dataset
uspto-grants-1998_04
Patent number
US05744611

Reaction notes

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