Sodium borohydride → HCID 86677889, compound

HRID 1499964Notes

Reaction equation

HRID 1499964 reaction equation
[C:1]([C:4]1[C:5]([O:18][CH2:19][CH3:20])=[C:6]([CH:12]2[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[C:7]([F:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:10][C:8]1[C:7]([F:11])=[C:6]([CH:12]2[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[C:5]([O:18][CH2:19][CH3:20])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86677888HCID 86677888, compound

Product 1

HCID 86677889HCID 86677889, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-Acetyl-5-chloro-2-ethoxy-6-fluorophenyl)-1,3-oxazolidin-2-one (175 mg, 0.58 mmol) was stirred in methanol (10 mL) at 0° C. and sodium tetrahydroborate (33 mg, 0.87 mmol) was added. The mixture was stirred at rt for 1 hour and evaporated. Water was added and the mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and evaporated to give an approximate 1:1 mixture of diastereomers, 175 mg, 99%. LCMS calculated for C13H15ClFNO4Na (M+Na)+: m/z=326.1; found: 326.1.

Workup

  1. customevaporated
  2. additionWater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give
  9. additionan approximate 1:1 mixture of diastereomers, 175 mg, 99%

Sources & evidence

ORD record
ord-988446a4843949b3972927b526fd08b0
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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