HCID 18629712, compound → HCID 21267692, compound

HRID 565184Notes

Reaction equation

HRID 565184 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([N+:19]([O-])=O)=[CH:13][C:12]=1[O:22][CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([NH2:19])=[CH:13][C:12]=1[O:22][CH3:23])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 18629712HCID 18629712, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21267692HCID 21267692, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

27 g (83 mmol) N-t-butoxycarbonyl-4-nitro-2,5-dimethoxyphenethylamine J3 was dissolved in 300 ml methanol, and 1.5 g 10% palladium on carbon black was added. This suspension was hydrogenated at 2.2 atm. for 18 hours till no further hydrogen uptake was observed. The catalyst was filtered off and the solvent was evaporated to afford 22.3 g white powder (yield: 98%). 1H-NMR (CDCl3), δ (ppm): 1.40 (s, 9H), 1.55 (s, 2H), 2.65 (t, 2H), 3.25 (t, 2H), 3.70 (s, 3H), 3.80 (s, 31H), 6.30 (s, 1H), 6.58 (s, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-90189f31c19f45179604b3d028940aea
Source dataset
uspto-grants-2001_01
Patent number
US06171866B2

Reaction notes

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