Pyrrolidine → HCID 71599104, compound

HRID 925629Notes

Reaction equation

HRID 925629 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[C:22]([CH3:23])=[CH:21][C:20]([C:24]([O:26]C)=O)=[C:19]4[CH3:28])=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]4[C:22]([CH3:23])=[CH:21][C:20]([C:24]([N:29]5[CH2:33][CH2:32][CH2:31][CH2:30]5)=[O:26])=[C:19]4[CH3:28])=[CH:14][CH:13]=3)[CH2:9][CH2:10]2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 71599016HCID 71599016, compound

Product 1

HCID 71599104HCID 71599104, compound

Conditions

Temperature
100 °C

Procedure

A mixture of the methyl 1-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}-2,5-dimethyl-1H-pyrrole-3-carboxylate (0.06 g) synthesized in Example 4 and pyrrolidine (0.112 g) was stirred in a sealed tube at 100° C. for 16 hours. The reaction mixture was left to cool to room temperature and concentrated under reduced pressure; the resulting residue was purified by silica gel column chromatography (NH preparative silica gel plate 0.5 mm; eluent: n-hexane/ethyl acetate=50/50) to give the titled compound as a colorless solid.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto cool to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (NH preparative silica gel plate 0.5 mm; eluent: n-hexane/ethyl acetate=50/50)

Sources & evidence

ORD record
ord-c917dd6094524c7fa157753e39647e87
Source dataset
uspto-grants-2016_03
Patent number
US09284324B2

Reaction notes

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