rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate → rac-tert-Butyl 1-(3-{[cyclopentyl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

HRID 626453Notes

Reaction equation

HRID 626453 reaction equation
[C:1]1([CH:6]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][CH3:35])[CH2:30][CH2:29]2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][C:26]=2[F:27])[CH2:13][C:14]2([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pt](=O)=O>[CH:1]1([CH:6]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][CH3:35])[CH2:30][CH2:29]2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][C:26]=2[F:27])[CH2:13][C:14]2([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][CH2:16]2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 90014967rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

Product 1

HCID 118106687rac-tert-Butyl 1-(3-{[cyclopentyl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

20.7 mg (0.04 mmol) of rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate were initially charged in 3 ml of methanol, 3 mg (0.01 mmol) of platinum(IV) oxide were added and the mixture was hydrogenated at RT and standard pressure for 5 h. The mixture was then filtered through kieselguhr, the residue was washed thoroughly with methanol and the filtrate was concentrated under reduced pressure. 19.5 mg (100% purity, 94% of theory) of the title compound were obtained.

Workup

  1. customwas hydrogenated at RT
  2. filtrationThe mixture was then filtered through kieselguhr
  3. washthe residue was washed thoroughly with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b606b398cac54aa98288a87936f19806
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

Loading…