Pyridine → HCID 23093552, compound

HRID 1022317Notes

Reaction equation

HRID 1022317 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1.[C:19](Cl)(=[O:23])[O:20][CH2:21][CH3:22]>C(OCC)(=O)C>[C:19](=[O:23])([O:20][CH2:21][CH3:22])[O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 23093552HCID 23093552, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl 3-hydroxypropylcarbamate (8.00 g) obtained in Reference Example 40 and ethyl acetate (50 mL) were added pyridine (4.06 mL) and ethyl chlorocarbonate (5.95 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 sodium sulfate. Concentration under reduced pressure gave the title compound (9.31 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 sodium sulfate
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-1586b1d1bc0c4a3ea10f999e77cbc007
Source dataset
uspto-grants-2014_05
Patent number
US08722084B2

Reaction notes

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