Sodium Azide → N-[(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-yl]methanesulfonamide

HRID 722273Notes

Reaction equation

HRID 722273 reaction equation
[CH3:1][S:2]([NH:5][C@@H:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@@H:7]1OS(C)(=O)=O)(=[O:4])=[O:3].[N-:20]=[N+]=[N-].[Na+]>CC(N(C)C)=O.CCOC(C)=O>[NH2:20][C@@H:7]1[CH2:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:6]1[NH:5][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86590533HCID 86590533, compound

Product 1

HCID 67220650N-[(1R,2R)-2-Amino-2,3-dihydro-1H-inden-1-yl]methanesulfonamideYield 84.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

(1R,2S)-1-Methanesulphonamido-2-methylsulphonyloxyindan (2.0 g, 6.56 mmol) was dissolved in dry dimethyl acetamide (20 ml). Sodium azide (1.7 g, 26.2 mmol) was added and the mixture heated to 90° C. for 1 hour. The reaction was cooled, diluted with EtOAc (100 ml), washed with water (6×50 ml), dried over magnesium sulphate and filtered. 10% Palladium on activated carbon was added and the mixture stirred under a hydrogen atmosphere for 3 hours. Filtration through celite followed by evaporation gave the title compound (1.25 g, 83%) as a pale green solid.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water (6×50 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. addition10% Palladium on activated carbon was added
  6. filtrationFiltration through celite
  7. customfollowed by evaporation

Sources & evidence

ORD record
ord-8d1afeb7e34b4fd7afa0439f94dad712
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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