Sodium Azide → 2-Pyrrolidinone, 5-(azidomethyl)-, (5S)-

HRID 62553Notes

Reaction equation

HRID 62553 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([CH2:7]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:4][CH2:3]1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([CH2:7][C@H:5]1[NH:6][C:2](=[O:1])[CH2:3][CH2:4]1)=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2734055[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate

Product 1

HCID 713542382-Pyrrolidinone, 5-(azidomethyl)-, (5S)-Yield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A round bottom flask was charged with (S)-(5-oxopyrrolidin-2-yl)methyl-4-methylbenzenesulfonate (18.4 g, 68.5 mmol), DMF (400 mL), and NaN3 (17.8 g, 274 mmol). The resulting mixture was stirred at 55° C. for overnight. Removal of solvent under reduced pressure followed by flash chromatography purification (7% MeOH in CHCl3 as the eluent) provided the (S)-5-(azidomethyl) pyrrolidin-2-one (8.45 g, 60.36 mmol, 88%) as a yellow oil.

Workup

  1. customRemoval of solvent under reduced pressure
  2. customfollowed by flash chromatography purification (7% MeOH in CHCl3 as the eluent)

Sources & evidence

ORD record
ord-cfa990570e664226b90a6c90b3034ebc
Source dataset
uspto-grants-2016_09
Patent number
US09446393B2

Reaction notes

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