Methanol → HCID 21474716, compound

HRID 1901670Notes

Reaction equation

HRID 1901670 reaction equation
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([CH:15]([CH3:21])[C:16](OCC)=[O:17])[CH2:10]1.CO>O1CCCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([CH:15]([CH3:21])[CH2:16][OH:17])[CH2:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 21474732HCID 21474732, compound

Product 1

HCID 21474716HCID 21474716, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.4 g of lithium borohydride was added, whilst ice-cooling, to a solution of 2.95 g of ethyl 2-[5-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]propionate (prepared as described in Preparation 4) in 25 ml of tetrahydrofuran, and then a mixture of 0.37 ml of methanol and 5 ml of tetrahydrofuran was added dropwise to the resulting mixture. The reaction mixture was then stirred at room temperature for 2 hours. At the end of this time, the tetrahydrofuran was removed from the reaction mixture by evaporation under reduced pressure, and an aqueous solution of sodium chloride was added to the resulting residue, which was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The ethyl acetate was then removed from the extract by evaporation under reduced pressure, and the resulting residue was recrystallized from ethyl acetate, to give 0.93 g of the title compound, melting at 114° C. to 115° C.

Workup

  1. additionwas added dropwise to the resulting mixture
  2. customAt the end of this time, the tetrahydrofuran was removed from the reaction mixture by evaporation under reduced pressure
  3. additionan aqueous solution of sodium chloride was added to the resulting residue, which
  4. extractionwas then extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customThe ethyl acetate was then removed from the
  7. extractionextract by evaporation under reduced pressure
  8. customthe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4ad80ac4ef1f45a0b96ef955f38b2668
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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