Water → HCID 10821988, compound

HRID 2375448Notes

Reaction equation

HRID 2375448 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O>CN(C)C=O>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:18]=[N+:19]=[N-:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 118072543-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

Product 1

HCID 10821988HCID 10821988, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

The compound (3R)-1-benzyl-3-[(methylsulfonyl) oxy]pyrrolidine (1.3 g, 5.8 mM) was dissolved in dimethylformamide (25.0 ml) and sodium azide (1.5 g, 23.3 mM) was added to it. The reaction mixture was maintained at 90-100° C. for about 12 hours followed by cooling at room temperature. The reaction mixture was poured into cold water (150.0 ml) with constant stirring. The organic compound was extracted with ethyl acetate and washed with water and brine solution, dried over anhydrous sodium sulphate and concentrated to give the title compound. Yield=78% (0.9 g, 4.5 m. This material was used as such in the next step.

Workup

  1. temperatureby cooling at room temperature
  2. extractionThe organic compound was extracted with ethyl acetate
  3. washwashed with water and brine solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c6e1fedbf9214059a35da0a3c18e8997
Source dataset
uspto-grants-2008_12
Patent number
US07465751B2

Reaction notes

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