Sodium Azide → HCID 58869127, compound

HRID 2355219Notes

Reaction equation

HRID 2355219 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21]OS(C)(=O)=O)[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[N-:27]=[N+:28]=[N-:29].[Na+]>CN1C(=O)CCC1>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][N:27]=[N+:28]=[N-:29])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58869139HCID 58869139, compound

Product 1

HCID 58869127HCID 58869127, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methanesulfonic acid (R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl ester (2.0 g, 4.99 mmol) in 30 mL of NMP was added sodium azide (1.55 g, 0.024 mol). The reaction mixture was heated to 75° C. with stirring for two hours. The reaction was quenched by addition of water, and the resulting mixture was extracted with diethyl ether. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:EtOAc 3:2) to give 1.76 g (quantitative) of C—[(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-yl]-methyl azide.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (hexanes:EtOAc 3:2)

Sources & evidence

ORD record
ord-bb66819680464eb8b2e7db382a44c4c1
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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