Hydrochloric Acid → 7-Chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid

HRID 910161Notes

Reaction equation

HRID 910161 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([O:13]C)=[O:12])=[C:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4](=[O:15])[CH:3]=1.C1COCC1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4](=[O:15])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57689810Methyl 7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Product 1

HCID 534029727-Chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 1b (800 mg, 3.52 mmol) was stirred in a solution of THF (10 mL), MeOH (5 mL), and 1N NaOH (5 mL) at r.t. for 20 h. The solution was made acidic with 1N HCl and extracted (3×) with CHCl3. Organics were dried (MgSO4) and concentrated in vacuo to give 637 mg (85%) of compound 9a as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.17 (s, 1H), 6.43 (s, 1H), 3.99 (t, 2H, J=7.4 Hz), 3.32 (t, 2H, J=7.8 Hz), 1.95-2.21 (m, 2H). MS (ES) [m+H] calc'd for C9H8ClNO3, 214. found 214.

Workup

  1. extractionextracted (3×) with CHCl3
  2. dry with materialOrganics were dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d423458d6229415ebe08f2bfcaa34acf
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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