Acetaldehyde, 2,2-dimethoxy- → HCID 68159557, compound

HRID 445908Notes

Reaction equation

HRID 445908 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17][NH2:18])[CH2:6]2.[CH3:20][O:21][CH:22]([O:25][CH3:26])[CH:23]=O>C(O)C.O.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][N:14]([CH3:19])[CH2:15][CH2:16][CH2:17][NH:18][CH2:23][CH:22]([O:25][CH3:26])[O:21][CH3:20])[CH2:6]2

Participants

6

Reactant 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 68159697HCID 68159697, compound

Product 1

HCID 68159557HCID 68159557, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1 g (3.7 mmoles) of N-{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-N-methylpropane-1,3-diamine is dissolved in 20 mL of ethanol. 520 mg (0.45 mL) of a 60% solution of glyoxal 1,1-dimethyl acetal in water and then 100 mg of Pd/C 10% are added. The reaction mixture is hydrogenated at atmospheric pressure and ambient temperature for 12 hours. The catalyst is filtered off and the filtrate is evaporated to dryness. 1.2 g of expected product are obtained in the form of an oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-9a59ccb9f96749499d0e2e4fc27a6af0
Source dataset
uspto-grants-2013_07
Patent number
US08476426B2

Reaction notes

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