Formaldehyde → HCID 53853843, compound

HRID 1789846Notes

Reaction equation

HRID 1789846 reaction equation
C=O.[CH2:3]([O:5][C:6](=[O:26])[CH:7]([CH:11]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[CH3:12])[C:8](O)=O)[CH3:4].C(NCC)C.CCOC(C)=O>C(Cl)Cl>[C:22]([O:21][C:19]([N:16]1[CH2:17][CH2:18][CH:13]([CH:11]([CH3:12])[C:7]([C:6]([O:5][CH2:3][CH3:4])=[O:26])=[CH2:8])[CH2:14][CH2:15]1)=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 54449227HCID 54449227, compound

Product 1

HCID 53853843HCID 53853843, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formaldehyde (132 mg, 1.65 mmol, 37% in water) was added to a solution of of crude 2-[1-(1-tert-butoxycarbonyl-piperidin4-yl)-ethyl]-malonic acid monoethyl ester (416 mg) in methylene chloride (2 mL) at 0° C. Diethylamine (153 μL, 1.47 mmol) was added dropwise and the mixture was stirred at room temperature over night. EtOAc was added and the mixture was washed with water and saturated NaHCO3, dried and concentrated under reduced pressure. The crude was purified by flash chromatography (toluene/EtOAc, 3:1) to give 4-(2-ethoxycarbonyl-1-methyl-allyl)-piperidine-1-carboxylic acid tert-butyl ester (0.18 g, 49% over two steps).

Workup

  1. washthe mixture was washed with water and saturated NaHCO3
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude was purified by flash chromatography (toluene/EtOAc, 3:1)

Sources & evidence

ORD record
ord-38d871a641174a1f87aebfb6a9fb8167
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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