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

HRID 344036Notes

Reaction equation

HRID 344036 reaction equation
O[C@H:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C@@H:3]1[C:14]([O:16][CH3:17])=[O:15]>[Pd].CO>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH2:5][CH2:4][C@H:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:2]2

Participants

4

Reactant 1

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

Product 1

HCID 22866788(S)-methyl (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)formateYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (1R,2S)-methyl [1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthyl]formate (2.22 g) and 10% palladium on carbon in methanol (50 ml) was stirred under hydrogen (2-3 atm) at room temperature for 22 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give (S)-methyl (5-methoxy-1,2,3,4-tetrahydro-2-naphthyl)formate as a colorless oil (1.66 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-86df12bd5a974a0fa76e1bfdf4288294
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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