Triethylamine → HCID 178472454, compound

HRID 470699Notes

Reaction equation

HRID 470699 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:20][Si:21]([CH3:36])([CH3:35])[CH2:22][CH2:23][O:24][C:25](ON1C(=O)CCC1=O)=[O:26]>O1CCOCC1.O>[CH3:20][Si:21]([CH3:36])([CH3:35])[CH2:22][CH2:23][O:24][C:25]([NH:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 178472434HCID 178472434, compound

Product 1

HCID 178472454HCID 178472454, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl trans-4-aminocyclohexanecarboxylate (J. Med. Chem., 1971, 14, 600-614) (29.5 g, 143 mmol) was dissolved in 1,4-dioxane (290 ml) and water (290 ml), triethylamine (30.0 ml, 215 mmol) and 1-[2-(trimethylsilyl)ethoxycarbonyloxy]pyrrolidine-2,5-dione (40.8 g, 157 mmol) were added under ice cooling and the resulting mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated and then the residue was diluted with ethyl acetate and washed with 10% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine in that order. The organic layer was dried over anhydrous sodium sulfate and the solvent was concentrated under reduced pressure to give 44.3 g (98%) of the title compound as colorless needle-like crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with 10% aqueous citric acid solution, saturated sodium bicarbonate solution, and brine in that order
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6aa9c9252ff14453a70ea5920a304210
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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