Sodium Azide → HCID 86609135, compound

HRID 902351Notes

Reaction equation

HRID 902351 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[C:17]([Cl:23])=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])[C:17]([Cl:23])=[CH:18][CH:19]=2)[O:14]1)=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609136HCID 86609136, compound

Product 1

HCID 86609135HCID 86609135, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ((2R)-7-chloro-8-o-tolylchroman-2-yl)methyl 4-methylbenzenesulfonate (0.8 g, 1.8 mmol) in DMSO (50 mL) was added sodium azide (1.2 g, 18.4 mmol) and the resulting mixture was heated at 60° C. overnight. The mixture was extracted with ethyl acetate, washed with water and saturated sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of 0 to 20% ethyl acetate in hexanes provided 0.5 g (88%) of (2R)-2-(azidomethyl)-7-chloro-8-o-tolylchroman as a colorless oil.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water and saturated sodium chloride
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by ISCO

Sources & evidence

ORD record
ord-cef1c182e53a4ae283d52b6714334175
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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