2,4-Difluorobenzaldehyde → HCID 89650467, compound

HRID 1479024Notes

Reaction equation

HRID 1479024 reaction equation
C(O[K])(C)(C)C.F[C:8]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][C@H:26]([OH:30])[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCOCC1.O>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH2:27][C@H:26]([O:30][C:8]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:9]=2[CH:10]=[O:11])[CH2:25]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 737702,4-DifluorobenzaldehydeHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 178418922HCID 178418922, compound

Product 1

HCID 89650467HCID 89650467, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

tBuOK (434 mg; 3.87 mmol; 1.1 eq.) was added to a solution of 2,4-difluoro-benzaldehyde (500 mg; 3.52 mmol; 1 eq.) and (S)-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (779 mg; 3.87 mmol; 1.1 eq.) in 1,4-dioxane (3 mL) and reaction mixture was stirred at room temperature for 15 minutes. The solution was diluted with water and extracted with DCM. The organic layer was dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (heptanes/EA) afforded the title compound (208 mg, 18%) as white solid. HPLC (max plot) 92.8%; Rt 4.46 min.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (heptanes/EA)

Sources & evidence

ORD record
ord-f4d5aa20bbc24c808258d72e5ca94bcb
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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