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

HRID 627226Notes

Reaction equation

HRID 627226 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]([CH2:27][CH3:28])=[CH:19]1)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][CH:18]1[CH2:23][NH:22][C@@H:21]([C:24]([NH2:26])=[O:25])[C:20]([CH2:27][CH3:28])=[CH:19]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 89852009(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-ethyl-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 89852076(R)-5-(allyloxyamino)-3-ethyl-1,2,5,6-tetrahydropyridine-2-carboxamideYield 74.3%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-ethyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 213, 0.87 g, 2.12 mmol) following the procedure described for Intermediate 12. Silica gel chromatography (0%-8% methanol/dichloromethane) afforded the title compound (0.355 g, 74.3%) as an off-white solid upon drying on high-vacuum.

Sources & evidence

ORD record
ord-3ce2feb0143b46f3b4931fc9be4d8e1c
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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