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

HRID 627255Notes

Reaction equation

HRID 627255 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]([CH:27]2[CH2:29][CH2:28]2)=[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>>[CH2:1]([O:4][NH:5][CH:18]1[CH2:23][NH:22][C@@H:21]([C:24]([NH2:26])=[O:25])[C:20]([CH:27]2[CH2:28][CH2:29]2)=[CH:19]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89852178(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-cyclopropyl-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 89852304(R)-5-(allyloxyamino)-3-cyclopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide

Procedure

The title compound was prepared from (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-cyclopropyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 243, 0.518 g, 1.23 mmol) following the procedure described for Intermediate 12. The desired product was obtained as a light yellow oil (0.171 g, 59%). The product is a mixture of diastereomers.

Sources & evidence

ORD record
ord-3fa1fc2ce12d41eebf7f85a7a41a6f67
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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