Pyridine → HCID 45092271, compound

HRID 2096053Notes

Reaction equation

HRID 2096053 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](OC(=O)C)(=[O:21])[CH3:20]>C(OCC)(=O)C>[C:19]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:12])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 45092271HCID 45092271, compoundYield 84.1%

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 acetic anhydride (5.13 g), and stirred at room temperature for 21 hrs. To the reaction solution was added ethyl acetate (200 mL), and washed with water (100 mL), aqueous solution of copper sulfate (40 mL), water (60 mL) and saturated brine (60 mL), followed by drying over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to give title compound as colorless oil (8.34 g).

Workup

  1. washwashed with water (100 mL), aqueous solution of copper sulfate (40 mL), water (60 mL) and saturated brine (60 mL)
  2. dry with materialby drying over anhydrous sodium sulfate
  3. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f710c3b70abd4362a8c5e9bf134e345b
Source dataset
uspto-grants-2013_05
Patent number
US08449911B2

Reaction notes

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