(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide → O-allyl-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)-methyl)-4-(prop-1-en-2-yl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine

HRID 627108Notes

Reaction equation

HRID 627108 reaction equation
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([C:24]([CH3:26])=[CH2:25])=[CH:22][C@@H:21]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[NH:20][CH2:19]1)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[C:23]([C:24]([CH3:26])=[CH2:25])=[CH:22][C@@H:21]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 89851806(2R,5R)-5-(allyloxyamino)-4-methyl-1,2,5,6-tetrahydropyridine-2-carboxamideHCID 89852508N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide2×

Product 1

HCID 131735282O-allyl-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)-methyl)-4-(prop-1-en-2-yl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine

Procedure

The desired product was prepared from N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-(prop-1-en-2-yl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide (Intermediate 55, 2.45 g, 4.68 mmol) following the procedure described for Intermediate 22. The desired product was obtained as yellow oil (1.19 g, 75%).

Sources & evidence

ORD record
ord-7cd13ff755bb42d9aaff2d5f1d2e4c55
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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