Methanol → 6-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile

HRID 1499938Notes

Reaction equation

HRID 1499938 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:13]=[C:12]([Cl:14])[C:9]([C:10]#[N:11])=[C:8]([CH:15]2[O:19][C:18](=[O:20])[NH:17][CH2:16]2)[C:7]=1[O:21][CH2:22][CH3:23])(=[O:5])[CH3:4].CO>>[Cl:14][C:12]1[C:9]([C:10]#[N:11])=[C:8]([CH:15]2[O:19][C:18](=[O:20])[NH:17][CH2:16]2)[C:7]([O:21][CH2:22][CH3:23])=[C:6]([CH:3]([OH:5])[CH3:4])[CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866778544-Acetyl-6-chloro-3-ethoxy-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile2×

Product 1

HCID 866778556-Chloro-3-ethoxy-4-(1-hydroxyethyl)-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile

Procedure

Sodium tetrahydroborate (19 mg, 0.50 mmol) was added to a mixture of 4-acetyl-6-chloro-3-ethoxy-2-(2-oxo-1,3-oxazolidin-5-yl)benzonitrile (100 mg, 0.34 mmol) (racemic mixture from step 3) in methanol (1.6 mL, 38 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 10 minutes and evaporated. The residue was diluted with ethyl acetate, washed with 1 N HCl, brine, dried over sodium sulfate, filtered and concentrated to give the desired compound as a mixture of four diastereomers, 58 mg, 55%. LCMS calculated for C14H16ClN2O4 (M+H)+: m/z=311.1; found: 311.1.

Workup

  1. customevaporated
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 1 N HCl, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6904dc4b6b4c4850aaccedb91018ce0f
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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