(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-cyclopropyl-2-oxobut-3-enyl)carbamate → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

HRID 627270Notes

Reaction equation

HRID 627270 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:13]([CH2:21][C:22](=[O:28])[C:23]([CH:25]1[CH2:27][CH2:26]1)=C)[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>>[Si:1]([O:8][CH2:9][C@@H:10]1[CH:11]=[C:23]([CH:25]2[CH2:26][CH2:27]2)[C:22](=[O:28])[CH2:21][N:13]1[C:14]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:20])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 89852359(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-cyclopropyl-2-oxobut-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 89852228(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-cyclopropyl-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Procedure

The title compound was prepared from (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-cyclopropyl-2-oxobut-3-enyl)carbamate (Intermediate 262, 5.16 g, 12.60 mmol) following the procedure described for Intermediate 7, except the reaction mixture was heated at 85° C. overnight The desired product was obtained as a light yellow oil (3.82 g, 79%).

Sources & evidence

ORD record
ord-a7cdac3ec19345e3aeee9a6eb82faddf
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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