Pyrrolidine → HCID 14043515, compound

HRID 868891Notes

Reaction equation

HRID 868891 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 62A (2.62 g, 12.77 mmol), acetone (26 mL), 3 Å molecular sieves (1.55 g), and pyrrolidine (0.211 ml, 2.55 mmol) were stirred at room temperature for 4 days. The mixture was concentrated then purified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient) to provide the title compound (1.52 g, 6.20 mmol, 49% yield). MS (DCI+) m/z 246 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthen purified by flash chromatography (SiO2, 0-50% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-79fe555a926346c6bae8d1dc4d3bee35
Source dataset
uspto-grants-2015_03
Patent number
US08969325B2

Reaction notes

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