Sodium Nitrite → (1S,2R)-(-)-1-Amino-2-indanol

HRID 1586308Notes

Reaction equation

HRID 1586308 reaction equation
C([C@H:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[OH:13])(O)=O.[N:14]([O-])=O.[Na+]>OS(O)(=O)=O>[NH2:14][C@H:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]1[OH:13]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 56974563HCID 56974563, compound

Product 1

HCID 9866743(1S,2R)-(-)-1-Amino-2-indanol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

The hydrazide of (1S,2R)-1-carboxy-2-hydroxyindane (0.5 gram) is reacted with a solution of 0.5 grams of sodium nitrite in 10 ml of 5% H2SO4. The reaction mixture is maintained for 1 hour at 0-5° C., followed extraction of the reaction mixture with ethyl acetate, followed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether, drying of the extracts over MgSO4, filtration, and the removal of solvent by rotary evaporation. The product (1S,2R)-1-amino-2-indanol is isolated as a light yellow oil.

Workup

  1. extractionextraction of the reaction mixture with ethyl acetate
  2. extractionfollowed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether
  3. dry with materialdrying of the extracts over MgSO4, filtration
  4. customthe removal of solvent
  5. customby rotary evaporation

Sources & evidence

ORD record
ord-c8b9db35bf02447ab019f9fd5a4fe3ca
Source dataset
uspto-grants-1999_08
Patent number
US05942644

Reaction notes

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