Ethyl bromoacetate → HCID 22914679, compound

HRID 1377680Notes

Reaction equation

HRID 1377680 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 22380697tert-Butyl 4-(2-hydroxyanilino)piperidine-1-carboxylate

Product 1

HCID 22914679HCID 22914679, compound

Procedure

To a stirred 0° C. solution of 1-t-Butyloxycarbonyl-4-(2-hydroxyphenylamino)piperidine (5.2 g, 18 mmol) from Step 1 was added NaH (800 mg of a 60% suspension in mineral oil, 20 mmol). After 30 min, ethyl bromoacetate (2.2 mL, 20 mmol) was added and the reaction was warmed to ambient temperature and stirred for 2 h. The reaction was quenched by the addition of acetic acid (1 mL), and the solvents were removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 20% EtOAc-hexanes as eluant. 1-t-Butyloxycarbonyl-4-((2-ethoxycarbonylmethoxyphenyl)amino)piperidine was obtained as an oil (90% yield).

Workup

  1. customThe reaction was quenched by the addition of acetic acid (1 mL)
  2. customthe solvents were removed under reduced pressure
  3. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-33a134c52cca4acc8dd4ab9c77da6181
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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