HCID 89852058, compound → (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-1,2,3,6-tetrahydro-pyridine-4-carboxamide

HRID 627147Notes

Reaction equation

HRID 627147 reaction equation
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([C:24]([NH2:26])=[O:25])=[CH:22][C@@H:21]([CH2:27][O:28][CH3:29])[NH:20][CH2:19]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(ON[C@@H]1C(C(N)=O)=C[C@@H](CO[Si](C(C)(C)C)(C)C)NC1)C=C.C(ON([C@@H]1C(C(N)=O)=C[C@@H](CO[Si](C(C)(C)C)(C)C)NC1)S(C1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O)(=O)=O)C=C>>[CH2:1]([O:4][NH:5][C@@H:18]1[C:23]([C:24]([NH2:26])=[O:25])=[CH:22][C@@H:21]([CH2:27][O:28][CH3:29])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 89852058HCID 89852058, compound2×HCID 89852509(3R,6S)-3-(N-(allyloxy)-2,4-dinitrophenylsulfonamido)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridine-4-carboxamideHCID 89852545(3R,6S)-3-(allyloxyamino)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridine-4-carboxamide

Product 1

HCID 89852143(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-1,2,3,6-tetrahydro-pyridine-4-carboxamide

Procedure

This intermediate was prepared from (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 113, 734 mg, 1.36 mmol) using the same procedure and isolation techniques to prepare Intermediate 107 from Intermediate 106. The title compound was an orange oil (173 mg, 53%).

Sources & evidence

ORD record
ord-6c1b09798cf74edfa03c45a290077c0a
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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