rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(3,4-dihydroisoquinolin-2(1H)-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate → rac-tert-Butyl 1-(3-{[cyclopentyl(3,4-dihydroisoquinolin-2(1H)-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

HRID 626454Notes

Reaction equation

HRID 626454 reaction equation
[C:1]1([CH:6]([N:28]2[CH2:37][CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[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[CH2:37][CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[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])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 118106768rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(3,4-dihydroisoquinolin-2(1H)-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

Product 1

HCID 118106672rac-tert-Butyl 1-(3-{[cyclopentyl(3,4-dihydroisoquinolin-2(1H)-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

102 mg (0.2 mmol, purity 72%) of rac-tert-butyl 1-(3-{[cyclopent-1-en-1-yl(3,4-dihydroisoquinolin-2(1H)-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate were initially charged in 14.4 ml of methanol, 14.4 mg (0.06 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. This gave 102 mg (purity 36%) of the title compound which was reacted further without purification.

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
  5. customThis gave 102 mg (purity 36%) of the title compound which was reacted further without purification

Sources & evidence

ORD record
ord-852d3569250a4f72973eb72288f08f0c
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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