2-Methyl-2-butene → HCID 89650335, compound

HRID 1479050Notes

Reaction equation

HRID 1479050 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]([C:38]([F:41])([F:40])[F:39])[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]([C:38]([F:41])([F:39])[F:40])[CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 89650060HCID 89650060, compound

Product 1

HCID 89650335HCID 89650335, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (219 mg; 2.42 mmol; 5 eq.) and sodium dihydrogenphosphate (233 mg; 1.94 mmol; 4 eq.) in water (1 mL) was added dropwise to a mixture of 2-methyl-2-butene (1 mL) and 4-(2-formyl-phenoxy)-3-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester (181 mg; 0.48 mmol; 1 eq.) in 1,4-dioxane (4 mL). The reaction mixture was stirred at room temperature for 1 hour and the 1,4-dioxane concentrated in vacuo. The aqueous solution was diluted with water and the pH made acidic with 0.1M HCl. The mixture was extracted with DCM (2×) and the combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (86 mg, 46%) as a white solid. HPLC (max plot) 97.3%, Rt 4.39 min. UPLC/MS: (MS−) 388.3 ([M−H]−).

Workup

  1. concentrationthe 1,4-dioxane concentrated in vacuo
  2. additionThe aqueous solution was diluted with water
  3. extractionThe mixture was extracted with DCM (2×)
  4. dry with materialthe combined organic phase was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by mass

Sources & evidence

ORD record
ord-ce961b82052443d8ab43245756c1b277
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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