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)-3,4-dimethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627205Notes

Reaction equation

HRID 627205 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:14]([CH2:22][C:23](=[O:27])[C:24](C)=[CH2:25])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11](C)=[CH2:12])([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>>[Si:1]([O:8][CH2:9][C@@H:10]1[C:11]([CH3:12])=[C:24]([CH3:25])[C:23](=[O:27])[CH2:22][N:14]1[C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 89852373tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 131735289(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate2×

Product 1

HCID 89852083(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3,4-dimethyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylateYield 69.1%

Conditions

Temperature
115 °C

Procedure

The title compound was prepared from (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-methylbut-3-en-2-yl(3-methyl-2-oxobut-3-enyl)carbamate (Intermediate 189, 3.72 g, 9.36 mmol) following the procedure described for Intermediate 7 except the reaction mixture was heated at 110-120° C. for 48 hours and doubling the catalyst loading (0.6 equivalents). Silica gel chromatography (0%-15% ethyl acetate/hexanes) afforded the desired product as a light tan oily solid (2.39 g, 69%).

Sources & evidence

ORD record
ord-2259e84a102f48c881d18f23ca3831ec
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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