tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylate → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-isopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627092Notes

Reaction equation

HRID 627092 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22](=[O:28])[C:23](=C)[CH:24]([CH3:26])[CH3:25])[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].[Si](OC[C@@H]1C=C(C)C(=O)CN1C(OC(C)(C)C)=O)(C(C)(C)C)(C)C>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:11]=[C:23]([CH:24]([CH3:25])[CH3:26])[C:22](=[O:28])[CH2:21][N:13]1[C:14]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:20])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 89852373tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 131735279(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(4-methyl-3-methylene-2-oxopentyl)carbamate2×

Product 1

HCID 89852363(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-isopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalyst

Procedure

The title compound was prepared from (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(4-methyl-3-methylene-2-oxopentyl)carbamate (Intermediate 34, 0.839 g, 2.04 mmol) following the procedure described for Intermediate 7, using 0.32 eq of (1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium. The desired product was obtained as a colorless oil (0.667 g, 85%).

Sources & evidence

ORD record
ord-3c7f7f44db314a149ab0ff7fae386281
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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