Water → HCID 23114295, compound

HRID 2376414Notes

Reaction equation

HRID 2376414 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:28])=[C:16]([NH:21][C:22](=[O:27])[C:23](=[O:26])[CH2:24][CH3:25])[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[OH:26][CH:23]([CH2:24][CH3:25])[C:22]([NH:21][C:16]1[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]2[O:12][CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=3)[C:14]=2[C:15]=1[CH3:28])=[O:27]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23114371HCID 23114371, compound

Product 1

HCID 23114295HCID 23114295, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3-(4-isopropylphenyl)-4,6,7-trimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxobutanamide obtained in Example 17 (237 mg, 0.62 mmol) in methanol (5 mL) was added sodium borohydride (24 mg, 0.62 mmol) at 0° C. and the resulting mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution and the product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to obtain 170 mg (yield: 72%) of the title compound. Melting point: 146-147° C.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4d4c9b07bd654b03b429f0eaf57d0b3a
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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