N-(allyloxy)-N-((3R,6S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide → O-allyl-N-((3R,6S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine

HRID 627287Notes

Reaction equation

HRID 627287 reaction equation
[CH2:1]([O:4][N:5]([C@@H:18]1[CH:23]=[C:22]([CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C@@H:21]([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[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)=C[C@@H](CO[Si](C(C)(C)C)(C)C)NC1)C=C>CO.ClCCl>[CH2:1]([O:4][NH:5][C@@H:18]1[CH:23]=[C:22]([CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:31])[CH3:32])([CH3:28])[CH3:29])[C@@H:21]([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:37])[CH3:38])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 89852205N-(allyloxy)-N-((3R,6S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide2×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 131735304O-allyl-N-((3R,6S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamineYield 86%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared from N-(allyloxy)-N-((3R,6S)-5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-6-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide (Intermediate 283, 6.49 g, 10.11 mmol) according to the procedure described for Intermediate 12. Silica gel chromatography (0%-5% methanol/dichloromethane) afforded the desired product (3.95 g, 86%) as a yellow oil.

Sources & evidence

ORD record
ord-2951360c1dd042379bb95059534ff87d
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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