Methanol → HCID 59485031, compound

HRID 1850493Notes

Reaction equation

HRID 1850493 reaction equation
CO.[CH3:3][C:4]1([CH3:31])[CH2:8][C:7]2[C:9]([CH3:30])=[C:10]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1.[BH4-].[Na+]>O>[CH3:31][C:4]1([CH3:3])[CH2:8][C:7]2[C:9]([CH3:30])=[C:10]([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]([OH:29])[CH3:28])=[CH:25][CH:26]=4)[CH2:17][CH2:16]3)[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59485021HCID 59485021, compound

Product 1

HCID 59485031HCID 59485031, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the methanol (1.0 mL) solution of 1-{4-[4-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazin-1-yl]phenyl}ethanone (39 mg, 0.10 mmol) synthesized in Example 95, sodium borohydride (11 mg, 0.30 mmol) was added under ice cooling. The mixture was stirred for 2 hours. The reaction solution was added with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was removed by distillation under reduced pressure. The resulting residue was crystallized from hexane to obtain the title compound 24 mg (yield 60%). Melting point was 133 to 136° C. (hexane-ethyl acetate).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was crystallized from hexane

Sources & evidence

ORD record
ord-db10b79ec0044f518dd43c892702d6b3
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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