Pyridine → HCID 59769522, compound

HRID 2096051Notes

Reaction equation

HRID 2096051 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](OC(=O)C)(=[O:22])[CH3:21]>C(OCC)(=O)C>[C:20]([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])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 545141tert-Butyl N-(4-hydroxybutyl)carbamate

Product 1

HCID 59769522HCID 59769522, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of tert-butyl 4-hydroxybutylcarbamate (3.83 g) obtained in Reference Synthetic Example 35 and ethyl acetate (20 mL) were added pyridine (1.80 mL) and acetic anhydride (2.27 g), and stirred at room temperature for 19 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 (4.55 g).

Workup

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

Sources & evidence

ORD record
ord-4bdcbeaade4e4a879b1160f50374aa09
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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