HCID 89525845, compound → HCID 89524833, compound

HRID 1621014Notes

Reaction equation

HRID 1621014 reaction equation
[C:1]([C:3]1([C:7]2[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2]>CCO.[Pd]>[C:1]([C:3]1([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:4][CH2:5][CH2:6]1)#[N:2]

Participants

4

Reactant 1

HCID 89525845HCID 89525845, compound

Product 1

HCID 89524833HCID 89524833, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The solution of Example 265B (0.8 g, 3.2 mmol) in EtOH (15 mL) was hydrogenated in the presence of Pd/C (320 mg). The resulting mixture was stirred at room temperature for 12 hours. After the filtration to remove Pd/C, the filtrate was concentrated under reduced pressure to give title compound (780 mg, 92% yield) as a colorless oil, which was used in the next step without further purification. 1H NMR: (400 MHz, CDCl3): δ 3.68-3.38 (m, 2H), 3.33-3.03 (m, 2H), 2.77-2.33 (m, 3H), 2.26-2.12 (m, 2H), 1.90-1.62 (m, 4H), 1.49 (s, 9H).

Workup

  1. filtrationAfter the filtration
  2. customto remove Pd/C
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f870abc76691475e9189ff7cca547658
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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