HCID 70819237, compound → HCID 86680967, compound

HRID 331521Notes

Reaction equation

HRID 331521 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][N:10]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:5][CH:4]=1>ClCCl.O=[Mn]=O>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:12][CH2:11][N:10]2[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 70819237HCID 70819237, compound

Product 1

HCID 86680967HCID 86680967, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Di tert-butyl 2-[4-(hydroxymethyl)phenyl]piperazine-1,4-dicarboxylate (750 mg, 1.911 mmol) was dissolved in dichloromethane (12.00 mL) and dioxomanganese (1.993 g, 396.5 μL, 22.93 mmol) was added. The reaction was stirred at ambient temperature for 22 hours. Reaction followed by TLC. Reaction mixture was filtered through a pad of celite and washed with dichloromethane. Purified by column chromatography (ISCO Companion, 40 g column) dry loaded and eluted with 5 to 50% ethyl acetate/petroleum ether. Product fractions were combined and concentrated in vacuo to give the sub-title product. (699 mg, 94% yield). 1H NMR (400.0 MHz, CDCl3) δ 1.43-1.47 (m, 18H), 3.01 (br s, 2H), 3.43-3.44 (m, 1H), 3.98-4.01 (m, 2H), 4.44 (br s, 1H), 5.32 (br s, 1H), 7.49-7.51 (m, 2H), 7.87 (d, 2H) and 10.03 (s, 1H) ppm; TLC (petroleum ether: ethyl acetate, 1:1 v/v) Rf=0.61

Workup

  1. customReaction
  2. customReaction mixture
  3. filtrationwas filtered through a pad of celite
  4. washwashed with dichloromethane
  5. customPurified by column chromatography (ISCO Companion, 40 g column)
  6. customdry
  7. washeluted with 5 to 50% ethyl acetate/petroleum ether
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9ddb44f4097488984a53e0c8501d5a3
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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