Acetic Acid → HCID 29940585, compound

HRID 1789843Notes

Reaction equation

HRID 1789843 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH:25]=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].N1CCCCC1.C(O)(=O)C>C(Cl)Cl.CCOC(C)=O>[CH2:10]([O:9][C:1](=[O:8])[C:2](=[CH:25][CH:22]1[CH2:23][CH2:24][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:18])[CH2:20][CH2:21]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 29940585HCID 29940585, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl malonate (710 μL, 4.7 mmol) and 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 g,4.7 mmol) in methylene chloride (5 mL) was added piperidine (46 μL, 0.47 mmol) and acetic acid (27 μL, 0.47 mmol). The reaction mixture was stirred for 72 h at room temperature and then for 16 h at 45° C. EtOAc was added and the mixture was washed with water and brine, dried and concentrated under reduced pressure. The crude was purified by flash chromatography (heptane/EtOAc, 3:1→1:3) to give 2-(1-tert-butoxycarbonyl-piperidin4-ylmethylene)-malonic acid diethyl ester (0.69 g 40%).

Workup

  1. waitfor 16 h at 45° C
  2. washthe mixture was washed with water and brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by flash chromatography (heptane/EtOAc, 3:1→1:3)

Sources & evidence

ORD record
ord-a05c56976b414edf8d5d8980bc7e38dc
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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