(S,E)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-yl(2-oxopent-3-enyl)carbamate → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627248Notes

Reaction equation

HRID 627248 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:16]([CH2:24][C:25](=[O:29])/[CH:26]=C/C)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]([CH:13]1[CH2:15][CH2:14]1)=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]([CH:13]2[CH2:15][CH2:14]2)=[CH:26][C:25](=[O:29])[CH2:24][N:16]1[C:17]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:23])([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 89851850(S,E)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-yl(2-oxopent-3-enyl)carbamate2×HCID 89852373tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 89851848(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Conditions

Temperature
110 °C

Procedure

The title compound was prepared from (S,E)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-cyclopropylbut-3-en-2-yl(2-oxopent-3-enyl)carbamate (Intermediate 236, 4 g, 9.44 mmol) following the procedure described for Intermediate 7, except the reaction mixture was heated at 110° C. overnight. The desired product was obtained as a light brown oil (2.97 g, 82%).

Sources & evidence

ORD record
ord-779babc490194b6c968d5554fcfa78ca
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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