Ethyl Acetate → (1S,2R)-(-)-1-Amino-2-indanol

HRID 1586309Notes

Reaction equation

HRID 1586309 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](C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>O1CCCC1>[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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15696259HCID 15696259, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One gram of the hydroxamic acid of (1R,2S)-1-carboxy-2-hydroxyindane is reacted with equimolar amounts of diethyl azodicarboxylate and triphenylphosphine in tetrahydrofuran at room temperature using the procedure of Bittner, Grinberg and Kartoon (Tet. Lett. 23, 1965-8 (1974)). The product is isolated by acidification and 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. extractionfollowed by basification of the resulting aqueous solution with NaOH, extraction with methyl t-butyl ether
  2. dry with materialdrying of the extracts over MgSO4, filtration
  3. customthe removal of solvent
  4. customby rotary evaporation

Sources & evidence

ORD record
ord-71c422bdc4df404f81fdc13682b71a47
Source dataset
uspto-grants-1999_08
Patent number
US05942644

Reaction notes

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