(2S,5R)-5-(allyloxyamino)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide → (2S,5R)-6-(allyloxy)-3,4-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627213Notes

Reaction equation

HRID 627213 reaction equation
[CH2:1]([O:4][NH:5][C@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([NH2:14])=[O:13])[C:8]([CH3:15])=[C:7]1[CH3:16])[CH:2]=[CH2:3].[CH2:17]([O:20]N1C(=O)N2C[C@H]1C(C)=C[C@H]2CO[Si](C(C)(C)C)(C)C)C=C>>[CH2:1]([O:4][N:5]1[C:17](=[O:20])[N:10]2[CH2:11][C@H:6]1[C:7]([CH3:16])=[C:8]([CH3:15])[C@H:9]2[C:12]([NH2:14])=[O:13])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89851793(2S,5R)-5-(allyloxyamino)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×HCID 89852160(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,6-diazabicyclo[3.2.1]oct-3-en-7-one

Product 1

HCID 89852291(2S,5R)-6-(allyloxy)-3,4-dimethyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamideYield 66.5%

Procedure

The title compound was prepared from (2S,5R)-5-(allyloxyamino)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 197, 0.31 g, 1.38 mmol) following the procedure described for Intermediate 13. Silica gel chromatography (0%-70% ethyl acetate/hexanes) afforded the desired product as a white solid (0.23 g, 66.5%).

Sources & evidence

ORD record
ord-bf63a63a3a8946db90fdd0dbcf9e1e39
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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