Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate → tert-Butyl 4-(5-methylthiophen-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1477639Notes

Reaction equation

HRID 1477639 reaction equation
FC(F)(F)S(O[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:30]2[CH:34]=[C:33]([CH3:35])[S:32][CH:31]=2)O1>>[CH3:35][C:33]1[S:32][CH:31]=[C:30]([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:9][CH:8]=2)[CH:34]=1

Participants

3

Reactant 2

HCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 590070884,4,5,5-tetraMethyl-2-(5-Methylthiophen-3-yl)-1,3,2-dioxaborolane

Product 1

HCID 117840131tert-Butyl 4-(5-methylthiophen-3-yl)-5,6-dihydropyridine-1(2H)-carboxylateYield 69.4%

Procedure

tert-Butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-5,6-dihydropyridine-1(2H)-carboxylate (1.66 g, 5.00 mmol) and a crude product of 4,4,5,5,-tetramethyl-2-(5-methylthiophen-3-yl)-1,3,2-dioxaborolane (3.40 g) were used to obtain a crude product of the title compound (970 mg) by synthesis in a similar manner to Reference Synthesis Example 139.

Sources & evidence

ORD record
ord-a42b601b8606434aba8bd95661410244
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…