HCID 20027801, compound → HCID 57308969, compound

HRID 1722839Notes

Reaction equation

HRID 1722839 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[O:16][C:15](=[O:17])[CH:14]=[C:13]2[CH3:18])=[CH:8][CH:7]=1>C(OCC)(=O)C.O=[Pt]=O>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[O:16][C:15](=[O:17])[CH2:14][C@H:13]2[CH3:18])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 20027801HCID 20027801, compound

Product 1

HCID 57308969HCID 57308969, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The lactone from Example 10 (26 g) was hydrogenated in ethyl acetate (200 ml) over PtO2 (1 g) at 20 p.s.i. H2 pressure for 30 minutes. The mixture was filtered, concentrated and the residue was purified by chromatography on silica gel to Provide the title compound as an oil, contaminated with 7% of the (5S, 4S), (5R, 4R) diastereomer as determined by NMR spectroscopy.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-986d9faad3234a709ef1d9267b732269
Source dataset
uspto-grants-1989_08
Patent number
US04857659

Reaction notes

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