Aldoxime → HCID 57486351, compound

HRID 749135Notes

Reaction equation

HRID 749135 reaction equation
[CH:1](=[N:3][OH:4])[CH3:2].ClN1C(=O)CCC1=O.[C:13]([C:15]1[CH:21]2[CH2:22][CH:18]([CH2:19][N:20]2[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][CH:16]=1)#[CH:14].C(N(CC)CC)C>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH3:2][C:1]1[CH:14]=[C:13]([C:15]2[CH:21]3[CH2:22][CH:18]([CH2:19][N:20]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][CH:16]=2)[O:4][N:3]=1

Participants

7

Reactant 4

HCID 7863AldoximeHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 57485790HCID 57485790, compound

Product 1

HCID 57486351HCID 57486351, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6212ChloroformSolvent2×

Procedure

To a solution of acetaldoxime (65 mg, 1.1 mmol) in 15 mL of chloroform were added 2 drops of pyridine, followed by N-chlorosuccinimide (146 mg, 1.1 mmol). After stirring the cloudy mixture for 1 h at ambient temperature, tert-butyl 4-ethynyl-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate (233 mg, 1.00 mmol) was added in 2 mL of chloroform, followed by drop-wise addition of triethylamine (0.175 mL, 1.25 mmol). The mixture was stirred at ambient temperature for 4 h and then concentrated to dryness under reduced pressure. The residue was chromatographed on a silica gel column, with a gradient of 2:1 hexane/ethyl acetate to 2:1 ethyl acetate/hexane, to give first recovered starting material, then tert-butyl 4-(3-methyl-5-isoxazolyl)-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate (100 mg, 40%).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 4 h
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue was chromatographed on a silica gel column, with a gradient of 2:1 hexane/ethyl acetate to 2:1 ethyl acetate/hexane
  4. customto give first
  5. customrecovered

Sources & evidence

ORD record
ord-78c5d066bc374a9b94ad4f0e47e02f91
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Reaction notes

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