(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide → (2S,5R)-5-(allyloxyamino)-4-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627099Notes

Reaction equation

HRID 627099 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])[CH:20]=[C:19]1[CH:27]([CH3:29])[CH3:28])S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(ON[C@H]1CN[C@@H](C(N)=O)C=C1C)C=C>>[CH2:1]([O:4][NH:5][C@H:18]1[CH2:23][NH:22][C@H:21]([C:24]([NH2:26])=[O:25])[CH:20]=[C:19]1[CH:27]([CH3:29])[CH3:28])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89851806(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamideHCID 89852368(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×

Product 1

HCID 89852129(2S,5R)-5-(allyloxyamino)-4-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Procedure

The title compound was prepared from (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-4-isopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 41, 0.247 g, 0.58 mmol) following the procedure described for Intermediate 22. The desired product was obtained as a light yellow solid (98 mg, 71%)

Sources & evidence

ORD record
ord-d258e28e7e1648129661c9c69647bcdf
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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