Pyridine → HCID 23093479, compound

HRID 1022315Notes

Reaction equation

HRID 1022315 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].N1C=CC=CC=1.[C:20](Cl)(=[O:24])[O:21][CH2:22][CH3:23]>C(OCC)(=O)C>[C:20](=[O:24])([O:21][CH2:22][CH3:23])[O:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamate

Product 1

HCID 23093479HCID 23093479, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl 4-hydroxybutylcarbamate (3.71 g) obtained in Reference Example 35 and ethyl acetate (20 mL) were added pyridine (1.71 mL) and ethyl chlorocarbonate (2.55 g) under ice-cooling, and the mixture was stirred at room temperature for 24 hrs. Ethyl acetate (100 mL) was added to the reaction mixture, and the mixture was washed with water (50 mL), an aqueous copper sulfate solution (30 ml), water (30 mL) and saturated brine (30 mL) and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave the title compound (4.92 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with water (50 mL)
  3. dry with materialan aqueous copper sulfate solution (30 ml), water (30 mL) and saturated brine (30 mL) and dried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c272005e21594f9085f725af53419385
Source dataset
uspto-grants-2014_05
Patent number
US08722084B2

Reaction notes

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