Pyridine → HCID 23093552, compound

HRID 2096054Notes

Reaction equation

HRID 2096054 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 Synthetic Example 40 and ethyl acetate (50 mL) were added pyridine (4.06 mL) and ethyl chlorocarbonate (5.95 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 sodium sulfate. The solution was concentrated under reduced pressure to give title compound as colorless oil (9.31 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 sodium sulfate
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ff16364b074a42c1bb636602a1a2f302
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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