Thiophenol → (2S,5R)-5-(allyloxyamino)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide

HRID 627130Notes

Reaction equation

HRID 627130 reaction equation
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][NH:22][C@H:21]([C:24]([NH2:26])=[O:25])[C:20]([CH3:27])=[CH: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[CH2:23][NH:22][C@H:21]([C:24]([NH2:26])=[O:25])[C:20]([CH3:27])=[CH:19]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 89852088(2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide2×

Product 1

HCID 89852283(2S,5R)-5-(allyloxyamino)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamideYield 70.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxamide (Intermediate 84, 2.01 g, 5.07 mmol) and potassium carbonate (2.172 g, 15.72 mmol) in acetonitrile (10 mL) was added benzenethiol (1.557 mL, 15.21 mmol) and stirred at rt for 2 h. The solvent was evaporated at 30° C., redissolved in DCM and a little bit MeOH, filtered and loaded onto silica gel at 30° C. The crude mixture was purified via flash chromatography (220 g column, 0-20% MeOH/DCM), the fractions were concentrated at 35° C. and dried under high-vacuum to obtain the desired product (0.759 g, 70.9%) as an off-white solid.

Workup

  1. customThe solvent was evaporated at 30° C.
  2. dissolutionredissolved in DCM
  3. filtrationa little bit MeOH, filtered
  4. customloaded onto silica gel at 30° C
  5. customThe crude mixture was purified via flash chromatography (220 g column, 0-20% MeOH/DCM)
  6. concentrationthe fractions were concentrated at 35° C.
  7. customdried under high-vacuum

Sources & evidence

ORD record
ord-6fc6e477ad7042dc92221cd4aa3264e1
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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