Methanol → Tert-butyl 2-(4-methoxy-4-oxobutyl)piperidine-1-carboxylate

HRID 2388716Notes

Reaction equation

HRID 2388716 reaction equation
[C:1]([O-:4])([OH:3])=O.[Na+].Cl.[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].ClC[C:22](=O)[CH2:23][C:24](OCC)=O.O.[CH3:31]O>>[C:23]([O:3][C:1]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])=[O:4])([CH3:22])([CH3:24])[CH3:31]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 69484Ethyl 4-chloroacetoacetateHCID 516892Sodium BicarbonateHCID 66772062Methyl 4-(piperidin-2-yl)butanoate hydrochloride

Product 1

HCID 57904248Tert-butyl 2-(4-methoxy-4-oxobutyl)piperidine-1-carboxylateYield 55%

Procedure

NaHCO3 (35.1 g, 418 mmol) was added to a suspension of 2-aminophenol (2, 30.4 g, 279 mmol) and ethyl 4-chloro-3-oxobutanoate (1, 45.9 g, 279 mmol) in MeOH (280 ml) and the reaction mixture was stirred at room temperature for 2 days. After the addition of H2O (280 ml), the reaction mixture was extracted with Et2O (2×), washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography (silica, heptane/EtOAc, 6:1) to yield 3 (33.71 g, 55%).

Workup

  1. extractionthe reaction mixture was extracted with Et2O (2×)
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica, heptane/EtOAc, 6:1)

Sources & evidence

ORD record
ord-98128b319233424c977c8f5340a60a17
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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