Hydrochloric Acid → 7-Chloro-6-fluoro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acid

HRID 910146Notes

Reaction equation

HRID 910146 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])[C:3]=1[F:16].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])[C:3]=1[F:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57689809Methyl 7-chloro-6-fluoro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Product 1

HCID 576898127-Chloro-6-fluoro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 1c (460 mg, 1.9 mmol) was stirred in a solution of THF (10 mL), MeOH (5 mL), and 1N NaOH (5 mL) at RT 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 380 mg (88%) of compound 1d as a white solid. 1H NMR (400 MHz, CDCl3): δ 4.15 (t, 2H, J=7.6 Hz), 3.31 (t, 2H, J=7.6 Hz), 2.19-2.27 (m, 2H). MS (ES) [m+H] calc'd for C9H7ClFNO3, 232, 234. found 232, 234.

Workup

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

Sources & evidence

ORD record
ord-a349c3e7b6c446b59283d74a2ce50f18
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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