(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide → (2S,5R)-5-(allyloxyamino)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627212Notes

Reaction equation

HRID 627212 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][NH:22][C@H:21]([C:24]([NH2:26])=[O:25])[C:20]([CH3:27])=[C:19]1[CH3:28])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(ON[C@@H]1C(C)=C[C@@H](CO[Si](C(C)(C)C)(C)C)NC1)C=C>CO.ClCCl>[CH2:1]([O:4][NH:5][C@H:18]1[CH2:23][NH:22][C@H:21]([C:24]([NH2:26])=[O:25])[C:20]([CH3:27])=[C:19]1[CH3:28])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 89852316(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×HCID 131735277(3R,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-N-(prop-2-en-1-yloxy)-1,2,3,6-tetrahydropyridin-3-amine

Product 1

HCID 89851793(2S,5R)-5-(allyloxyamino)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamideYield 68.9%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3,4-dimethyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 196, 0.82 g, 2.00 mmol) following the procedure described for Intermediate 12. Silica gel chromatography (0%-10% methanol/dichloromethane) afforded the desired product as a white solid (0.31 g, 68.9%).

Sources & evidence

ORD record
ord-939770f0832446699dd7134848e5cbf4
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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