Tributylvinyltin → 1-tert-butyl 2-methyl (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 1360110Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]=[C:5]2[O:18][C@H:19]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]([O:33][CH3:34])=[O:32])[CH2:20]1.[CH:35]([Sn](CCCC)(CCCC)CCCC)=[CH2:36]>C1(C)C=CC=CC=1>[C:12]1([C:7]2[CH:6]=[C:5]([O:18][C@H:19]3[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[C@H:21]([C:31]([O:33][CH3:34])=[O:32])[CH2:20]3)[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH:35]=[CH2:36])[CH:3]=3)[N:8]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-tert-butyl 2-methyl (2S,4R)-4-[(6-bromo-2-phenylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate 24 (1.45 g, 2.75 mmol) in toluene (20 mL) was added vinyltributyltin (0.96 mL, 3.3 mmol) and tetrakis-triphenylphosphine palladium (318 mg, 0.27 mmol). The mixture was then heated to 110° C. for 3 h, at which time, LC-MS revealed the disappearance of starting material. The reaction mixture was concentrated and purified on silica gel (gradient elution 15% to 50% EtOAc in hexanes) to give 1-tert-butyl 2-methyl (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate 25 (0.74 g, 56% yield) as a yellow solid. LRMS (M+H)+ Calcd.: 475. found 475.

Workup

concentrationThe reaction mixture was concentrated
custompurified on silica gel (gradient elution 15% to 50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-a78e2d01ae244c87b3a7e6258418aecb
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879797B2

Reaction notes

Loading…