Hydrochloric Acid → Methyl (4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]-L-prolinate hydrochloride

HRID 1879272Notes

Reaction equation

HRID 1879272 reaction equation
[CH2:1](C([SnH3])=C(CCCC)CCCC)[CH2:2]CC.Br[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH3:28])[N:23]=[C:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:21]=[C:20]2[O:35][C@H:36]1[CH2:40][N:39](C(OC(C)(C)C)=O)[C@H:38]([C:48]([O:50][CH3:51])=[O:49])[CH2:37]1.[ClH:52]>C1(C)C=CC=CC=1.O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[ClH:52].[CH3:28][O:27][C:26]1[CH:25]=[C:24]2[C:19]([C:20]([O:35][C@H:36]3[CH2:40][NH:39][C@H:38]([C:48]([O:50][CH3:51])=[O:49])[CH2:37]3)=[CH:21][C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:23]2)=[CH:18][C:17]=1[CH:1]=[CH2:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21115800Tri(butyl)vinylstannaneHCID 58005143HCID 58005143, compound

Product 1

HCID 66895937Methyl (4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]-L-prolinate hydrochloride

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Tributylvinylstannane (1.15 eq.) and tetrakis(triphenylphosphine) palladium(0) (0.07 eq.) were added to a solution of compound 116 in toluene (0.09 M) and the reaction mixture was heated at 100° C. After 20 h volatiles were removed in vacuo and the residue was purified by column chromatography (SiO2, PE:EtOAc with EtOAc from 1 to 60%) to give a pale yellow solid, that was taken up in a 4N solution of HCl in dioxane (0.31 M). The reaction mixture was stirred for 1 h and the resulting white solid recovered by filtration, washed with EtOAc/petroleum ether affording the title compound 117 (99%) as a pale yellow solid. MS (ES+) m/z 405 (M+H)+.

Workup

  1. customAfter 20 h volatiles were removed in vacuo
  2. customthe residue was purified by column chromatography (SiO2, PE:EtOAc with EtOAc from 1 to 60%)
  3. customto give a pale yellow solid, that
  4. filtrationthe resulting white solid recovered by filtration
  5. washwashed with EtOAc/petroleum ether affording the title compound 117 (99%) as a pale yellow solid

Sources & evidence

ORD record
ord-b93e61a4bce544909c3354bae241c2d0
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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