Ethyl Acetate → (1R,2S)-methyl [1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthyl]formate

HRID 963727Notes

Reaction equation

HRID 963727 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:14]([O:16][CH3:17])=[O:15])[C:8]2=[O:13].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C(OCC)(=O)C>CO>[OH:13][C@H:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][C@@H:7]1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 190824592-Methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 15547174(1R,2S)-methyl [1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthyl]formateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl [5-methoxy-1-oxo-1,2,3,4-tetrahydro-2-naphthyl]formate (2.50 g), D-10-camphorsulfonic acid (124 mg), [RuCl2 (S)-binap]2NEt3 (90 mg) [cf. Tetrahedron Letters, Vol. 35, No. 26, pp 4559-4562, 1994], ethyl acetate (23.8 ml) and methanol (1.25 ml) was stirred under hydrogen (90 atm) at 50° C. for 40 hours. The reaction mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give (1R,2S)-methyl [1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthyl]formate (2.47 g) as a white powder. mp: 87°-88° C.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-d9a652f235c045c581e6cf9e815f5e73
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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