2-Methyl-2-butene → HCID 89649830, compound

HRID 1479025Notes

Reaction equation

HRID 1479025 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][CH2:26][C@H:25]([O:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[CH:37]=[O: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][CH2:26][C@H:25]([O:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[C:37]([OH:6])=[O: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 89650467HCID 89650467, compound

Product 1

HCID 89649830HCID 89649830, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium chlorite (320 mg; 3.54 mmol; 5.5 eq.) and sodium dihydrogenphosphate (278 mg; 2.32 mmol; 3.6 eq.) in water (2 mL) was added dropwise to a mixture of 2-methyl-2-butene (0.64 mL) and (S)-3-(5-fluoro-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (208 mg; 0.64 mmol; 1 eq.) in 1,4-dioxane (2 mL). The reaction mixture was stirred at room temperature for 16 hours 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 to afford the title compound (202 mg, 93%) as a white solid. HPLC (max plot) 94.3%; Rt 3.89 min. UPLC/MS: (MS−) 338.4 ([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

Sources & evidence

ORD record
ord-82b4a1901c694b31aadd7c704de10721
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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