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-ethyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylate

HRID 627219Notes

Reaction equation

HRID 627219 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:16]([CH2:24][C:25](=[O:29])C=CC)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]([CH2:14][CH3:15])=[CH:12]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>>[Si:1]([O:8][CH2:9][C@@H:10]1[C:11]([CH2:14][CH3:15])=[CH:12][C:25](=[O:29])[CH2:24][N:16]1[C:17]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89852373tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 131735293(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-ethylpent-3-en-2-yl(2-oxopent-3-enyl)carbamate2×

Product 1

HCID 89852241(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-ethyl-5-oxo-5,6-dihydropyridine-1 (2H)-carboxylateYield 54.2%

Conditions

Temperature
86 °C

Procedure

The title compound was prepared from (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-ethylpent-3-en-2-yl(2-oxopent-3-enyl)carbamate (Intermediate 206, 10.95 g, 25.72 mmol) according to the procedure described for Intermediate 7, except the reaction was heated at 86° C. for 6 days. Silica gel chromatography (0-10% ethyl acetate/hexanes) afforded the title compound (5.15 g, 54.1%) as a light yellow oil.

Sources & evidence

ORD record
ord-c10dc912ae0e44f8a0de247f1715ff92
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…