Thiophenol → (3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 627169Notes

Reaction equation

HRID 627169 reaction equation
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:29][O:30][CH3:31])[NH:20][CH2:19]1)S(C1C=CC=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:18]1[C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][C@@H:21]([CH2:29][O:30][CH3:31])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89851925(3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide2×

Product 1

HCID 89852322(3R,6S)-3-(allyloxyamino)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamideYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R,6S)-3-(N-(allyloxy)-2-nitrophenylsulfonamido)-6-(methoxymethyl)-N,N-dimethyl-1,2,3,6-tetrahydropyridine-4-carboxamide (Intermediate 141, 1.346 g, 2.96 mmol) and potassium carbonate (2.456 g, 17.77 mmol) in acetonitrile (50 mL) was added benzenethiol (1.825 mL, 17.77 mmol) and stirred at rt overnight. The solvent was evaporated then the crude mixture was redissolved in DCM and a little bit MeOH, filtered, loaded onto silica gel. The crude product was purified via flash chromatography (0-20% MeOH/DCM) and dried under high-vacuum to obtain the desired product (0.725 g, 91%) as a pale yellow oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude mixture was redissolved in DCM
  3. filtrationa little bit MeOH, filtered
  4. customThe crude product was purified via flash chromatography (0-20% MeOH/DCM)
  5. customdried under high-vacuum

Sources & evidence

ORD record
ord-089c902999b34e3c89b581ca21f6656f
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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