HCID 67378212, compound → 3'H-Spiro[azepane-4,1'-[2]benzofuran]

HRID 1182734Notes

Reaction equation

HRID 1182734 reaction equation
C([N:8]1[CH2:22][CH2:21][CH2:20][C:11]2([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[CH2:13][O:12]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:11]12([CH2:20][CH2:21][CH2:22][NH:8][CH2:9][CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][O:12]2

Participants

5

Reactant 2

HCID 67378212HCID 67378212, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 673663263'H-Spiro[azepane-4,1'-[2]benzofuran]Yield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (RS)-1-benzyl-3′H-spiro[azepane-4,1′-[2]benzofuran] (4.00 g, 13.6 mmol) in methanol (50 ml) in an autoclave was purged with argon. After addition of the palladium catalyst (10% Pd on activated charcoal, 1 g) the autoclave was pressurized with 5 bar of hydrogen gas. The mixture was stirred over night at room temperature. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate and aqueous sodium hydroxide solution (pH 14). The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give the title compound as white solid (2.5 g, 90%).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and aqueous sodium hydroxide solution (pH 14)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e61dc7e63a2643baa26baf26e56ff716
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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