Quinoline → Cyclopentyl(2S,4Z)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate

HRID 425032Notes

Reaction equation

HRID 425032 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]([O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:13])=[CH:4][CH:3]=1.N1C2C(=CC=CC=2)C=CC=1>[Pd]>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[CH2:10][C@H:11]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:12]([O:14][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 59243578Cyclopentyl(2S)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

Product 1

HCID 59243625Cyclopentyl(2S,4Z)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-enoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of cyclopentyl(2S)-5-(4-bromophenyl)-2-[(tert-butoxycarbonyl)amino]pent-4-ynoate (750 mg, 1.719 mmol), quinoline (41 μl, 3.44 mmol), 5% Pd on CaCO3 (500 mg) was purged with nitrogen. EtOH (60 ml) was added and the mixture was stirred under an atmosphere of H2 at room temperature for 21 hrs. Because of incomplete reaction, the mixture was filtered through Celite, treated with fresh catalyst (500 mg) and stirred under an atmosphere of H2 at room temp for a further 18 hrs. The mixture was filtered through Celite and the filtrate evaporated in vacuo to afford the crude product as a colourless oil. Column purification using 5% EtOAc/isohexane afforded the product (640 mg, 1.416 mmol, 82% yield) as a clear colourless oil. LCMS purity 97%: m/z 439 [M+H]+. 1H NMR showed 8 wt % trans-alkene.

Workup

  1. customwas purged with nitrogen
  2. additionEtOH (60 ml) was added
  3. customBecause of incomplete reaction
  4. filtrationthe mixture was filtered through Celite
  5. additiontreated with fresh catalyst (500 mg)
  6. stirringstirred under an atmosphere of H2 at room temp for a further 18 hrs
  7. filtrationThe mixture was filtered through Celite
  8. customthe filtrate evaporated in vacuo
  9. customto afford the crude product as a colourless oil
  10. customColumn purification

Sources & evidence

ORD record
ord-a3a6b86310134caa9db59b83b9cf728b
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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