2-Methyl-2-butene → HCID 89650493, compound

HRID 1479010Notes

Reaction equation

HRID 1479010 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].CC(=CC)C.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH:36]=[O:37])[CH:25]([F:38])[CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>O.O1CCOCC1>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([OH:6])=[O:37])[CH:25]([F:38])[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 89650378HCID 89650378, compound

Product 1

HCID 89650493HCID 89650493, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (274 mg; 3.03 mmol; 5 eq.) and sodium dihydrogen phosphate (291 mg; 2.42 mmol; 40 eq.) in water (4 mL) was added dropwise to a solution of 2-methyl-but-2-ene (0.5 mL) and 3-fluoro-4-(2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (196 mg; 0.61 mmol; 1 eq.) in 1,4-dioxane (4 mL) and the resulting mixture was stirred a room temperature for 3 hours. The dioxane was evaporated in vacuo and the pH made acidic with 1M HCl. The solution was extracted with ethyl acetate (2×), washed with brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound (205 mg, 100%) as a yellow oil. UPLC/MS: (MS−) 338.2 ([M−H]−).

Workup

  1. customThe dioxane was evaporated in vacuo
  2. extractionThe solution was extracted with ethyl acetate (2×)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a135d4abff8c4ee7b01df2e4ab354384
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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