HCID 89726545, compound → HCID 89726713, compound

HRID 926350Notes

Reaction equation

HRID 926350 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[O:10][CH2:9][CH2:8][N:7]1CC1C=CC=CC=1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[O:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 89726545HCID 89726545, compound

Product 1

HCID 89726713HCID 89726713, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the crude 4-benzyl-2-methyl-morpholine-3-carboxylic acid ethyl ester (Comp. No. 26) obtained in the preceding experiment in methanol (10 ml) was treated with a catalytic amount of palladium on charcoal (10% w/w; 25 mg). The flask was flushed with hydrogen and the hydrogen atmosphere was maintained whilst stirring at room temperature. After 5 h, the catalyst was removed by filtration, the solution was treated with a new amount of palladium on charcoal (10% w/w; 25 mg) and the hydrogen atmosphere was restored. Stirring was continued for a further 96 h. The catalyst was filtered off, washed with methanol and the combined filtrates were concentrated in vacuo to give 0.140 g of 2-methyl-morpholine-3-carboxylic acid ethyl ester, which was used in the next step without further purification. LC/MS (method 7): Rt=0.45 min; m/z=174.15 (M+H+).

Workup

  1. customThe flask was flushed with hydrogen
  2. temperaturethe hydrogen atmosphere was maintained
  3. customthe catalyst was removed by filtration
  4. additionthe solution was treated with a new amount of palladium on charcoal (10% w/w; 25 mg)
  5. stirringStirring
  6. waitwas continued for a further 96 h
  7. filtrationThe catalyst was filtered off
  8. washwashed with methanol
  9. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-6dc3a82e21ca4f8993cc9eb3a99a1f0a
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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