(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate → tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 627073Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22](=[O:26])[C:23]([CH3:25])=[CH2:24])[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])C=C)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.CC1C=C(C)C=C(C)C=1N1CCN(C2C(C)=CC(C)=CC=2C)C1=[Ru](Cl)(Cl)=CC1C=CC=CC=1OC(C)C>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:25]=[C:23]([CH3:24])[C:22](=[O:26])[CH2:21][N:13]1[C:14]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:20])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate (Intermediate 6, 26.18 g, 68.25 mmol) in toluene (600 mL) was purged with nitrogen for 15 minutes. (1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium (0.987 g, 1.57 mmol) was then added. The reaction mixture was heated at 65° C. for 1.5 hours. The reaction mixture was concentrated onto silica gel. Silica gel chromatography (0%-15% ethyl acetate/hexanes) afforded the desired product (21.18 g, 87%) as a colorless oil.

Workup

concentrationThe reaction mixture was concentrated onto silica gel

Sources & evidence

ORD record: ord-03254febe3a54b77a8d9f8eeb2629a00
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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