Water → HCID 68776240, compound

HRID 2263048Notes

Reaction equation

HRID 2263048 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23].O>O1CCCC1>[Cl:27][C:26]([Cl:29])([Cl:28])[CH2:25][O:24][C:22]([NH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 5458091-BOC-3-Aminopiperidine

Product 1

HCID 68776240HCID 68776240, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-aminopiperidine-1-carboxylate (1.00 g, 4.99 mmol) and pyridine (489 ml, 5.99 mmol) in tetrahydrofuran (16 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (0.829 ml, 5.99 mmol), and the mixture was stirred at room temperature for 1 hour. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was introduced to water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give 867 mg (46.2%) of the desired product as an oil.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. additionThe extract was introduced to water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-98115846be204637842918d12ed62f4f
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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