Sodium borohydride → HCID 23114129, compound

HRID 2376538Notes

Reaction equation

HRID 2376538 reaction equation
[C:1]([C:4]1[C:12]2[O:11][CH2:10][CH:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:8]=2[C:7]([CH3:22])=[C:6]([NH:23][C:24]([NH:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:5]=1[CH3:31])(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O>[C:27]([NH:26][C:24]([NH:23][C:6]1[C:5]([CH3:31])=[C:4]([CH:1]([OH:3])[CH3:2])[C:12]2[O:11][CH2:10][CH:9]([C:13]3[CH:14]=[CH:15][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:18]=3)[C:8]=2[C:7]=1[CH3:22])=[O:25])([CH3:29])([CH3:28])[CH3:30]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23114301HCID 23114301, compound

Product 1

HCID 23114129HCID 23114129, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of N-(7-acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-N′-(tert-butyl)urea (718 mg, 1.7 mmol) obtained in Example 204 in methanol (10 mL) was added sodium borohydride (64.3 mg, 1.7 mmol) at 0° C., and the resulting mixture was stirred for 3 hours. The reaction solution was diluted with water and the product was extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 115 mg (yield: 16%) of the title compound having high polarity of two isomers. Melting point: 212-214° C. (ethyl acetate-hexane).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ad8e4225eaff4f0db1385adc47ce63d6
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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