Triethylamine → HCID 53742937, compound

HRID 713434Notes

Reaction equation

HRID 713434 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.[C:18]([O:22][C:23](=[O:26])[CH2:24]Br)([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:24][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:26])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 424914Methyl isonipecotate

Product 1

HCID 53742937HCID 53742937, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of piperidine-4-carboxylic acid methyl ester (10 g, 70 mmol, 1 eq.) and Et3N (19.5 mL, 140 mmol, 2 eq.) in 150 mL of THF was added bromo-acetic acid tert-butyl ester (13.6 g, 70 mmol, 1 eq.) in 150 mL of THF. The resulting mixture was heated at reflux overnight. After 18 h, the resulting mixture was concentrated and purified by silica gel column chromatography (98/1/1 CH2Cl2/MeOH/NH4OH) to give the title compound as a yellow oil (0.84 g). Exact mass calculated for C13H24N1O4 258.2. MS (ESI) m/z 258.6 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationthe resulting mixture was concentrated
  4. custompurified by silica gel column chromatography (98/1/1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-f2775e66ee2b49c39b483c6df6235ad9
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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