Pyrrolidine → HCID 14043515, compound

HRID 536470Notes

Reaction equation

HRID 536470 reaction equation
[C:1]([C:4]1[C:5]([O-:14])=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[Na+].N1C[CH2:19][CH2:18][CH2:17]1>CC(C)=O>[CH3:17][C:18]1([CH3:19])[O:14][C:5]2=[N:6][C:7]([C:10]([F:12])([F:11])[F:13])=[CH:8][CH:9]=[C:4]2[C:1](=[O:3])[CH2:2]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86688228HCID 86688228, compound

Product 1

HCID 14043515HCID 14043515, compoundYield 243.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of Example 105A (2.62 g, 12.8 mmol), acetone (26 mL), 3 Å molecular sieves (1.55 g), and pyrrolidine (0.211 ml, 2.55 mmol) was stirred at ambient temperature for four days. The volatiles were removed in vacuo and the mixture was purified by flash column chromatography (SiO2, 0-50% EtOAc/hexanes gradient) provided the title compound (1.52 g, 6.20 mmol, 49% yield). MS (DCI+) m/z 246 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe mixture was purified by flash column chromatography (SiO2, 0-50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-0d195d0f19dd4f309e81d957fa114504
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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