Thiophenol → (3R,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-N-(prop-2-en-1-yloxy)-1,2,3,6-tetrahydropyridin-3-amine

HRID 627078Notes

Reaction equation

HRID 627078 reaction equation
[CH2:1]([O:4][N:5]([C@@H:18]1[C:23]([CH3:24])=[CH:22][C@@H:21]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[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]([CH3:24])=[CH:22][C@@H:21]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:28])[CH3:29])[NH:20][CH2:19]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89852702N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide2×

Product 1

HCID 131735277(3R,6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-N-(prop-2-en-1-yloxy)-1,2,3,6-tetrahydropyridin-3-amineYield 69.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(allyloxy)-N-((3R,6S)-6-((tert-butyldimethylsilyloxy)methyl)-4-methyl-1,2,3,6-tetrahydropyridin-3-yl)-2-nitrobenzenesulfonamide (Intermediate 11, 11.58 g, 23.27 mmol) and potassium carbonate (16.08 g, 116.34 mmol) in acetonitrile (200 mL) at room temperature was added benzenethiol (11.95 mL, 116.34 mmol). After 3 hours, the reaction mixture was concentrated to dryness and DCM was added. The resulting solids were removed by filtration. The filtrate was concentrated onto silica gel. Silica gel chromatography (0%-100% ethyl acetate/hexanes) afforded the desired product (5.06 g, 69.6%) as an orange oil.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness and DCM
  2. additionwas added
  3. customThe resulting solids were removed by filtration
  4. concentrationThe filtrate was concentrated onto silica gel

Sources & evidence

ORD record
ord-c81dd23e55b44c27beb9fe00af1ace52
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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