Ethyl Acetate → (1S,2S)-2-amino-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1586310Notes

Reaction equation

HRID 1586310 reaction equation
[OH:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@@H:3]1C(O)=O.[N:15](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>[OH:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@@H:3]1[NH2:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9442520HCID 9442520, compound

Product 1

HCID 6420130(1S,2S)-2-amino-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

One gram of the hydroxamic acid of (1S,2S)-1-hydroxy-2-carboxyteralin 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,2S)-1-hydroxy-2-aminotetralin 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-09e6b78baa304ea58cbe164ccf2cdba6
Source dataset
uspto-grants-1999_08
Patent number
US05942644

Reaction notes

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