Ammonium Hydroxide → HCID 53863445, compound

HRID 1789844Notes

Reaction equation

HRID 1789844 reaction equation
[Li][CH3:2].[CH2:3]([O:5][C:6](=[O:27])[C:7](=[CH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[NH4+].[OH-]>C1COCC1.[Cu]I>[CH2:3]([O:5][C:6](=[O:27])[CH:7]([CH:13]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:16][CH2:15]1)[CH3:2])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 29940585HCID 29940585, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 53863445HCID 53863445, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

MeLi (5.34 mL, 8.54 mmol, 1.6 M in diethyl ether) was added dropwise to a slurry of CuI (0.74 g, 3.88 mmol) in THF (5 mL) at −78° C. under argon and the mixture was stirred for 30 min. A solution of 2-(1-tert-butoxycarbonyl-piperidin4-ylmethylene)-malonic acid diethyl ester (0.69 g, 1.94 mmol) in THF (5 mL) was added dropwise and the reacton mixture was stirred for 120 min at −78° C. and was then allowed to warm to room temperature during 60 min. Concentrated aqueous NH4OH was added and the mixture was then extracted with EtOAc, washed with concentrated aqueous NH4OH and brine, dried and concentrated under reduced pressure. The crude was purified by flash chromatography (heptane/EtOAc, 3:1→1:6) to give 2-[1-(1-tert-butoxycarbonyl-piperidin-4-yl)-ethyl]-malonic acid diethyl ester (0.39 g, 54%).

Workup

  1. stirringthe reacton mixture was stirred for 120 min at −78° C.
  2. extractionthe mixture was then extracted with EtOAc
  3. washwashed with concentrated aqueous NH4OH and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by flash chromatography (heptane/EtOAc, 3:1→1:6)

Sources & evidence

ORD record
ord-1dc4c076a3904857b216076645d79004
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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