Sodium borohydride → HCID 118020562, compound

HRID 1777373Notes

Reaction equation

HRID 1777373 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:20]2[N:24]=[CH:23][CH:22]=[N:21]2)=[C:6]([CH:19]=1)[C:7]([N:9]1[CH2:13][CH2:12][O:11][CH:10]1[C:14](OCC)=[O:15])=[O:8].[BH4-].[Na+]>CO>[OH:15][CH2:14][CH:10]1[N:9]([C:7]([C:6]2[CH:19]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N:20]2[N:24]=[CH:23][CH:22]=[N:21]2)=[O:8])[CH2:13][CH2:12][O:11]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118201022HCID 118201022, compound

Product 1

HCID 118020562HCID 118020562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±)-ethyl 3-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,3-oxazolidine-2-carboxylate obtained in Reference Example 1 (4.0 g, 12.1 mmol) in MeOH (60 mL), NaBH4 (4.6 g, 121 mmol) was added gradually under cooling with ice water and stirred for 1 hour. The resulting mixture was heated to room temperature and stirred for 1 hour. The solvent was distilled off under reduced pressure, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was extracted with CHCl3. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over Na2SO4, then the drying agent was filtered off, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (HP-Sil 100 g, hexane/EtOAc=88/12 to 0/100) to obtain the title compound (3.6 g) (colorless oil).

Workup

  1. additionwas added gradually
  2. stirringstirred for 1 hour
  3. distillationThe solvent was distilled off under reduced pressure
  4. additiona saturated aqueous solution of ammonium chloride was added to the reaction mixture, which
  5. extractionwas extracted with CHCl3
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over Na2SO4
  8. filtrationthe drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe obtained residue was purified by column chromatography (HP-Sil 100 g, hexane/EtOAc=88/12 to 0/100)

Sources & evidence

ORD record
ord-b77589bcec714ef18f426eda7551c245
Source dataset
uspto-grants-2016_02
Patent number
US09266870B2

Reaction notes

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