Pyrrolidine → Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate

HRID 644216Notes

Reaction equation

HRID 644216 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23](F)[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:24]=[C:23]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 57602502Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate

Product 1

HCID 57602510Methyl 2-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate

Conditions

Temperature
80 °C

Procedure

The methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (7.99 mmol, 22.6 mmol) was diluted with pyrrolidine (18 mL, 215.6 mmol). The resulting mixture was heated to 80° C. After 3 hours, the reaction was cooled to room temperature and quenched with water (50 mL). The mixture was extracted with dichloromethane (200 mL). The organic layer was washed with saturated aqueous citric acid (3×50 mL), dried over sodium sulfate, filtered, and concentrated to a colorless oil (9.14 g, 22.6 mmol, 100%).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customquenched with water (50 mL)
  3. extractionThe mixture was extracted with dichloromethane (200 mL)
  4. washThe organic layer was washed with saturated aqueous citric acid (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-248ffb93d35e4ad4bcc2b7974ee386f9
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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