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

HRID 342910Notes

Reaction equation

HRID 342910 reaction equation
C[O:2][C:3]([CH:5]1[O:9][C:8](=[O:10])[NH:7][CH:6]1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.[BH4-].[Na+].O.Cl>C(O)C>[CH2:11]([C@H:6]1[C@@H:5]([CH2:3][OH:2])[O:9][C:8](=[O:10])[NH:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=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 the (4S,5S) and (4S,5R) isomers of 4-benzyl-2-oxo-oxazolidine-5-carboxylic acid methyl ester were added at 15°-20° over a period of 1.5 hours to a stirred solution of 20.8 g of sodium borohydride in 360 ml of ethanol and then stirred for a further 2 hours. The suspension was combined at 20° with 540 ml of water and the pH value adjusted to 7 with 165 ml of 3N hydrochloric acid. The suspension was stirred at room temperature for 2.5 hours, left to stand for 18 hours at 4° and then filtered. The residue was washed with water and dried and yielded 111.6 g (84%) of 99% (4S,5S)-4-benzyl-5-hydroxymethyl-oxazolidin-2-one, melting point 167.3°-168.9°, [α]D20 : -79.4° (1% in methanol).

Workup

  1. stirringThe suspension was stirred at room temperature for 2.5 hours
  2. waitleft
  3. waitto stand for 18 hours at 4°
  4. filtrationfiltered
  5. washThe residue was washed with water
  6. customdried

Sources & evidence

ORD record
ord-1b11f590db5a4b1ba35e02b94ff31fe2
Source dataset
uspto-grants-1999_01
Patent number
US05859248

Reaction notes

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