Sodium Azide → HCID 54553818, compound

HRID 2270103Notes

Reaction equation

HRID 2270103 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:9][CH2:8][C@H:7](OS(C)(=O)=O)[CH2:6]1)(=[O:3])[CH3:2].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[C:1]([O:4][C@@H:5]1[CH2:9][CH2:8][C@@H:7]([N:15]=[N+:16]=[N-:17])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 15407443HCID 15407443, compound

Product 1

HCID 54553818HCID 54553818, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a 8 ml DMF solution of 580 mg (2.61 mmol) of (1R,3S)-3-[(methylsulfonyl)oxy]cyclopentyl acetate, 203 mg (3.13 mmol) of sodium azide and 26 μl (0.13 mmol) of 15-crown-5-ether were added and stirred at 80° C. for 3 hours, followed by concentrating and then by diluting with 50 ml of diethyl ether. The residue was washed with 10 ml of saturated saline and then the solvent was distilled off to obtain 360 mg (82%) of the above-identified compound as a slightly brown oily substance.

Workup

  1. concentrationby concentrating
  2. additionby diluting with 50 ml of diethyl ether
  3. washThe residue was washed with 10 ml of saturated saline
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2e4acb985a454fb39abb7c9a576abc2d
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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