HCID 59485092, compound → HCID 59485001, compound

HRID 1850513Notes

Reaction equation

HRID 1850513 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]([CH3:35])=[C:17]([CH3:34])[C:18]4[O:22][C:21]([CH2:24][N:25]5[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]5)([CH3:23])[CH2:20][C:19]=4[C:32]=3[CH3:33])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.B.[Na]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[C:16]([CH3:35])=[C:17]([CH3:34])[C:18]4[O:22][C:21]([CH2:24][N:25]5[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]5)([CH3:23])[CH2:20][C:19]=4[C:32]=3[CH3:33])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 59485092HCID 59485092, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 59485001HCID 59485001, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethanol (2.0 mL) containing 1-({5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}methyl)piperidine-4-one (30 mg, 0.0628 mmol) synthesized in Example 132, sodium boron hydride (10 mg, 0.264 mmol) was added, and the mixture was stirred at room temperature for 1 hour. After that, the reaction solution was concentrated under reduced pressure, and the residue was distributed using ethyl acetate and water. The organic layer was washed with water and saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 65:35-0:100) and crystallized from ethyl acetate-hexane to give 15 mg of the title compound (yield 50%). Melting point was 139 to 143° C.

Workup

  1. additionwas added
  2. concentrationAfter that, the reaction solution was concentrated under reduced pressure
  3. washThe organic layer was washed with water and saturated saline
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 65:35-0:100)
  7. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9ffa6b20b65e4856a126992e0222c39b
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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