Thiophenol → O-allyl-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamine

HRID 627158Notes

Reaction equation

HRID 627158 reaction equation
[CH2:1]([O:4][N:5]([C@@H:21]1[CH:26]=[CH:25][C@@H:24]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[NH:23][CH2:22]1)S(C1C=CC([N+]([O-])=O)=CC=1[N+]([O-])=O)(=O)=O)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1>C(#N)C>[CH2:1]([O:4][NH:5][C@@H:21]1[CH:26]=[CH:25][C@@H:24]([CH2:27][O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[NH:23][CH2:22]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89852376N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2,4-dinitrobenzenesulfonamide2×

Product 1

HCID 89863150O-allyl-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)hydroxylamineYield 56.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-1,2,3,6-tetrahydropyridin-3-yl)-2,4-dinitrobenzenesulfonamide (Intermediate 127, 17.50 g, 33.10 mmol) and potassium carbonate (13.73 g, 99.31 mmol) in acetonitrile (700 mL), benzenethiol (5.10 ml, 49.65 mmol) was added. The reaction mixture was stirred at rt for 2.5 hours. LCMS showed the completion of the reaction. The reaction was concentrated, the diluted with EtOAc and filtered through a disposal filter. The filtrate was concentrated and the crude product was purified on silica gel column (0-4% MeOH in DCM) to get the desired product as a yellow oil (5.6 g).

Workup

  1. additionwas added
  2. customthe completion of the reaction
  3. concentrationThe reaction was concentrated
  4. additionthe diluted with EtOAc
  5. filtrationfiltered through a disposal
  6. filtrationfilter
  7. concentrationThe filtrate was concentrated
  8. customthe crude product was purified on silica gel column (0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-7f2dd51622c14f1889785e9d408f26a7
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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