HCID 67931226, compound → HCID 67931201, compound

HRID 982115Notes

Reaction equation

HRID 982115 reaction equation
C([O:8][CH2:9][C@@H:10]1[CH2:15][C:14]2[C:16]([O:21][CH3:22])=[CH:17][CH:18]=[C:19]([CH3:20])[C:13]=2[C@H:12]([CH2:23][Br:24])[O:11]1)C1C=CC=CC=1.[H][H]>[Pt].CO.C(OCC)(=O)C>[Br:24][CH2:23][C@H:12]1[C:13]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([O:21][CH3:22])[C:14]=2[CH2:15][C@@H:10]([CH2:9][OH:8])[O:11]1

Participants

6

Reactant 2

HCID 67931226HCID 67931226, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67931201HCID 67931201, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5% Platinum on carbon (1.0 g) is added to a solution of [1R,3S] 3-benzyloxymethyl-1-bromomethyl-3,4-dihydro-5-methoxy-8-methyl-1H-2-benzopyran (3.42 g, 8.7 mmol), from Step 2, in 150 mL of methanol and 5 mL of ethyl acetate. The reaction mixture is sealed under 4 atmospheres of hydrogen and shaken overnight. The reaction mixture is filtered to remove the catalyst and concentrated. The residue is purified by column chromatography on silica gel to give the title compound.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customto remove the catalyst
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0254c7a2ba044039861f67804cd6e4de
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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