Pyridine → HCID 23093479, compound

HRID 2096052Notes

Reaction equation

HRID 2096052 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) and ethyl acetate (20 mL) were added pyridine (1.71 g) and ethyl chlorocarbonate (2.25 g) under ice-cooling, and stirred at room temperature for 24 hrs. To the reaction solution was added ethyl acetate (100 mL), and washed with water (50 mL), aqueous solution of copper sulfate (30 mL), water (30 mL) and saturated brine (30 mL), followed by drying over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to give title compound as colorless oil (4.92 g).

Workup

  1. temperaturecooling
  2. washwashed with water (50 mL), aqueous solution of copper sulfate (30 mL), water (30 mL) and saturated brine (30 mL)
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c657bdc29794e9e8a486dbddb5c2429
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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