Potassium Hydroxide → HCID 21255139, compound

HRID 636564Notes

Reaction equation

HRID 636564 reaction equation
[OH-].[K+].[CH3:3][C:4]1[C:5]([C:19]([O:21]C)=[O:20])=[C:6]2[N:11]([C:12]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2>O.C(O)C>[CH3:3][C:4]1[C:5]([C:19]([OH:21])=[O:20])=[C:6]2[N:11]([C:12]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[CH2:10][CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21255184HCID 21255184, compound

Product 1

HCID 21255139HCID 21255139, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.46 g of potassium hydroxide pellets in 20 cm3 of water are added to a solution of 1.2 g of methyl 2-methyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylate in 20 cm3 of ethanol. The mixture is heated to reflux for 20 hours. The mixture is then concentrated at reduced pressure (2.7 kPa). The oily residue is taken up with 100 cm3 of water and washed with 4×20 cm3 of dichloromethane. The aqueous phase is filtered and then cooled and acidified with a 1N aqueous solution of hydrochloric acid to pH˜3-4. The solid is filtered off on a No. 4 glass sinter and washed with 4×30 cm3 of water. The solid obtained is recrystallized from 95 cm3 of a 60/40 ethanol/water mixture. 0.71 g of 2-methyl-3-(3-pyridyl)-5,6,7,8-tetrahydroindolizine-1-carboxylic acid are thus obtained in the form of a white powder melting at 250° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 20 hours
  3. concentrationThe mixture is then concentrated at reduced pressure (2.7 kPa)
  4. washwashed with 4×20 cm3 of dichloromethane
  5. filtrationThe aqueous phase is filtered
  6. temperaturecooled
  7. filtrationThe solid is filtered off on a No
  8. wash4 glass sinter and washed with 4×30 cm3 of water
  9. customThe solid obtained
  10. customis recrystallized from 95 cm3 of a 60/40 ethanol/water mixture

Sources & evidence

ORD record
ord-4731277b231a458ea35847c13345ca8e
Source dataset
uspto-grants-2001_02
Patent number
US06194426B1

Reaction notes

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