Sodium borohydride → HCID 59485028, compound

HRID 1850483Notes

Reaction equation

HRID 1850483 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:30])=[C:17]([C:27](=[O:29])[CH3:28])[C:18]4[O:22][C:21]([CH3:24])([CH3:23])[CH2:20][C:19]=4[C:25]=3[CH3:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+]>O.C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:30])=[C:17]([CH:27]([OH:29])[CH3:28])[C:18]4[O:22][C:21]([CH3:23])([CH3:24])[CH2:20][C:19]=4[C:25]=3[CH3:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 59485121HCID 59485121, compound

Product 1

HCID 59485028HCID 59485028, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the THF (1.5 ml)/methanol (1.5 ml) mixture solution of 1-{5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-7-yl}ethanone (120 mg, 0.294 mmol) synthesized in Example 80, sodium borohydride (133 mg, 3.52 mmol) was added and the mixture was stirred for 3 hours at room temperature. After diluting the reaction solution with water, THF and methanol in the reaction solution was removed by distillation under reduced pressure. The residue was extracted with ethyl acetate. The extract solution was washed with saturated brine, dried over anhydrous magnesium sulfate, and then solvent was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-80/20) and crystallized from ethyl acetate-hexane to obtain the title compound 60 mg (yield 50%). Melting point was 183 to 186° C.

Workup

  1. customwas removed by distillation under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe extract solution was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customsolvent was removed by distillation under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 99:1-80/20)
  7. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-8d6e8328034b41c697c64205412d2c3c
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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