Methanol → HCID 178497018, compound

HRID 2391738Notes

Reaction equation

HRID 2391738 reaction equation
[NH:1]1[C:9]2[CH2:8][C@@H:7]([C:10]([O:12][CH3:13])=[O:11])[NH:6][CH2:5][C:4]=2[N:3]=[CH:2]1.CO>O1CCOCC1.O=[Mn]=O>[CH3:13][O:12][C:10]([C:7]1[N:6]=[CH:5][C:4]2[N:3]=[CH:2][NH:1][C:9]=2[CH:8]=1)=[O:11]

Participants

5

Reactant 2

HCID 887MethanolHCID 178501028HCID 178501028, compound

Product 1

HCID 178497018HCID 178497018, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 59.9 g methyl (6S)-4,5,6,7-tetrahydro-imidazo[4,5-c]pyridine-6-carboxylate and 172.5 g MnO2 in 2 l anhydrous 1,4-dioxane is refluxed for 4 hours. The reaction mixture is allowed to come to 60-70° C. whereupon 1 l methanol is slowly added. The suspension is filtered hot and the filtrate is concentrated under reduced pressure to give a first batch of the title product. The filter cake is washed with hot methanol (2 l) and concentrated under reduced pressure to a volume of about 50 ml. 80 ml 1,4-dioxane is added whereupon precipitation takes place. After filtration a second batch of the title product is obtained. The washing procedure of the initial filter cakes is repeated once again to give a third batch of the title product.

Workup

  1. temperatureis refluxed for 4 hours
  2. additionis slowly added
  3. filtrationThe suspension is filtered hot
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c63c0bbab4264c0cbfcc59b711893fa0
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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