Hydrochloric Acid → 5,6,7,8-Tetrahydroindolizine-1-carboxylic acid

HRID 926364Notes

Reaction equation

HRID 926364 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][N:9]2[C:14]=1[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:5])C.O.[OH-].[K+].Cl>CO>[C:6]1([C:4]([OH:5])=[O:3])[CH:7]=[CH:8][N:9]2[C:14]=1[CH2:13][CH2:12][CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 12324173Ethyl 5,6,7,8-tetrahydroindolizine-1-carboxylate

Product 1

HCID 123241775,6,7,8-Tetrahydroindolizine-1-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid ethyl ester (2b) (3.0 g, 15.5 mmol) in methanol (46 ml) was added water (23 ml) and potassium hydroxide (6.4 g, 97 mmol) and the mixture was stirred at reflux until complete conversion according to LC/MS (ca. 3 h). 160 ml water was added the mixture was acidified with excess hydrochloric acid. The forming precipitate was filtered off, washed once with water and dried in vacuo to give 2.02 g (79%) of 5,6,7,8-tetrahydro-indolizine-1-carboxylic acid as white solid. LC/MS (method 5; MS ionization method ES−): Rt=3.08 min; m/z=164.06 (M−H−).

Workup

  1. temperatureat reflux until complete conversion
  2. customaccording to LC/MS (ca. 3 h)
  3. filtrationThe forming precipitate was filtered off
  4. washwashed once with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-72b8f638995e477495d527c3623a6d4b
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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