(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-oxopent-3-enyl)carbamate → (S)-Tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627103Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22](=[O:26])[CH:23]=CC)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:11]=C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:11]=[CH:23][C:22](=[O:26])[CH2:21][N:13]1[C:14]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:20])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-oxopent-3-enyl)carbamate (Intermediate 49, 27.0 g, 70.39 mmol) was dissolved in toluene (650 ml). The solution was purged with nitrogen for 15 minutes before the addition of Hoveyda-Grubbs Catalyst 2nd Generation (0.885 g, 1.41 mmol). The reaction mixture was heated under nitrogen at 65° C. After 2 hours LCMS showed complete formation of the product. The reaction mixture was concentrated under reduced pressure. Silica gel chromatography (10%-35% ethyl acetate/hexanes) afforded the desired product as a solid (17.0 g, 70%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record: ord-7e104608dace4da3b1cc22f68a8745ba
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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