Ethyl 4-(3-chloro-6-methoxyquinolin-2-yl)cyclohex-3-enecarboxylate → Ethyl 4-(3-chloro-6-methoxyquinolin-2-yl)cyclohexanecarboxylate

HRID 1410590Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:14]2[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16][CH:15]=2)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2>CCO>[Cl:1][C:2]1[C:3]([CH:14]2[CH2:15][CH2:16][CH:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:18][CH2:19]2)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 30 °C

Procedure

To ethyl 4-(3-chloro-6-methoxyquinolin-2-yl)cyclohex-3-enecarboxylate (900 mg, 2.60 mmol) in EtOH (40 mL) was added Rh(PPh3)3Cl (90.0 mg 0.0900 mmol). The mixture was stirred at 30° C. for 4 days under H2 (15 psi). The mixture was filtered off and the filtrate was concentrated to give the crude product, which was purified by silica gel column (PE/EtOAc=10/1) to give the desired product (234 mg, yield 26%).

Workup

filtrationThe mixture was filtered off
concentrationthe filtrate was concentrated
customto give the crude product, which
customwas purified by silica gel column (PE/EtOAc=10/1)

Sources & evidence

ORD record: ord-ab37f05a91184039ae3a081822fe1515
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921562B2

Reaction notes

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