Selectfluor → Methyl 7-chloro-6-fluoro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

HRID 910145Notes

Reaction equation

HRID 910145 reaction equation
[Cl:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4](=[O:15])[CH:3]=1.[B-](F)(F)(F)[F:17].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CN(C=O)C>[Cl:1][C:2]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]2[N:5]([CH2:6][CH2:7][CH2:8]2)[C:4](=[O:15])[C:3]=1[F:17]

Participants

4

Reactant 2

HCID 2724933Selectfluor2×HCID 57689810Methyl 7-chloro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate

Product 1

HCID 57689809Methyl 7-chloro-6-fluoro-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Compound 1b (1.36 g, 5.98 mmol) was stirred in DMF (10 mL) at 88° C. Selectfluor® (2.54 g, 7.17 mmol) in DMF (8 ml) was added dropwise, and the reaction stirred for 1 h. Additional Selectfluor® (1.2 g, 3.39 mmol) in DMF (5 mL) was added, and the reaction stirred 1 h longer. The solution was concentrated in vacuo and purified by silica gel chromatography (75% EtOAc/CH2Cl2) to give 460 mg (31%) of compound 1c as a white solid. 1H NMR (400 MHz, CDCl3): δ 4.18 (t, 2H, J=7.6 Hz), 3.86 (s, 3H), 3.37 (t, 2H, J=7.6 Hz), 2.20-2.28 (m, 2H). MS (ES) [m+H] calc'd for C10H9ClFNO3, 246, 248. found 246, 248.

Workup

  1. stirringthe reaction stirred 1 h longer
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by silica gel chromatography (75% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-d8cd16208b0840cab236a9af55627c45
Source dataset
uspto-grants-2011_09
Patent number
US08022057B2

Reaction notes

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