Sodium Azide → HCID 86600237, compound

HRID 2108786Notes

Reaction equation

HRID 2108786 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([CH2:13]OS(C)(=O)=O)[C@@H:10]([OH:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:13][C@@H:11]1[C@@H:10]([OH:19])[CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12]1)=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866002383-Pyrrolidinemethanol, 4-hydroxy-1-(phenylmethyl)-, 3-methanesulfonate, (3R,4R)-

Product 1

HCID 86600237HCID 86600237, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

(3R,4R)-1-Benzyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (835 mg), sodium azide (381 mg) and N,N-dimethylformamide (12 mL) were mixed together, and the mixture was stirred at 120° C. for 1 hour and was concentrated under reduced pressure. Water (10 mL) was then added to the resulting residue and the mixture was extracted with diethyl ether (2×30 mL). The diethyl ether layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate: methanol=20:1) to give (3R,4R)-3-azidomethyl-1-benzyl-4-hydroxypyrrolidine as a pale brown oil (576 mg).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionWater (10 mL) was then added to the resulting residue
  3. extractionthe mixture was extracted with diethyl ether (2×30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate: methanol=20:1)

Sources & evidence

ORD record
ord-b905bcdcd7d245f1962a1dd0ed0cd7b4
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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