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

HRID 1901964Notes

Reaction equation

HRID 1901964 reaction equation
[CH2:1]([CH:8]1[CH:12]([C:13](OC)=[O:14])[O:11][C:10](=[O:17])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>C(O)C>[CH2:1]([C@H:8]1[C@@H:12]([CH2:13][OH:14])[O:11][C:10](=[O:17])[NH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 13606585Methyl 4-benzyl-2-oxo-oxazolidine-5-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 g of the 98:2 mixture of (4S,5S) and (4S,5R) isomers of methyl 4-benzyl-2-oxo-oxazolidine-5-carboxylate from Example 7B) are added at 15°-20° C. over 1.5 hours to a stirred solution of 20.8 g of NaBH4 in 360 ml of ethanol and stirred for 2 hours. The suspension is treated with 540 ml of water at 20° C. and the pH is brought to 7 with 165 ml of 3N hydrochloric acid. The suspension is stirred at 22° C. for 2.5 hours, left to stand at 4° C. for 18 hours, then filtered and the residue is washed with water and dried to give 111.6 g (84%) of 99% (4S,5S)-4-benzyl-5-hydroxymethyl-oxazolidin-2-one, m.p. 167.3°-168.9° C., [α]D20 : -79.4° (1% in methanol).

Workup

  1. stirringThe suspension is stirred at 22° C. for 2.5 hours
  2. waitleft
  3. waitto stand at 4° C. for 18 hours
  4. filtrationfiltered
  5. washthe residue is washed with water
  6. customdried

Sources & evidence

ORD record
ord-9076d5b1cc4345d4a105f8b40044abd1
Source dataset
uspto-grants-1996_11
Patent number
US05578730

Reaction notes

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