Methanol → HCID 59191367, compound

HRID 626058Notes

Reaction equation

HRID 626058 reaction equation
[CH2:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[C:18](=[O:19])[CH2:17][CH2:16][C:15]3=[O:20])=[CH:10][C:9]=2[F:21])=[C:5]([O:24][CH3:25])[CH:4]=1)[CH3:2].CO.[BH4-].[Na+]>C(#N)C>[CH2:1]([C:3]1[CH:23]=[CH:22][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:20])[CH2:16][CH2:17][CH2:18][OH:19])=[CH:10][C:9]=2[F:21])=[C:5]([O:24][CH3:25])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59191285HCID 59191285, compound

Product 1

HCID 59191367HCID 59191367, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1-[4-(4-ethyl-2-methoxyphenoxy)-3-fluorophenyl]pyrrolidine-2,5-dione (169.8 mg, 0.49 mmol) was added methanol (2 mL). The reaction mixture was stirred for 1 h 30 at room temperature under argon. Acetonitrile (2 mL) and NaBH4 (190.7 mg, 4.9 mmol) were added to the reaction. The reaction mixture was stirred at 50° C. for 17 h. Then it was concentrated, dissolved in dichloromethane, washed with a saturated solution of NH4Cl and extracted with dichloromethane. Combined organic phases were dried over Na2SO4, concentrated in vacuo, to give the title product as a white solid used without further purification (169.5 mg; 100%).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. for 17 h
  2. concentrationThen it was concentrated
  3. dissolutiondissolved in dichloromethane
  4. washwashed with a saturated solution of NH4Cl
  5. extractionextracted with dichloromethane
  6. dry with materialCombined organic phases were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4c4001b8bce497d8f927925bcfc12ff
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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