HCID 86748310, compound → HCID 57126774, compound

HRID 1492011Notes

Reaction equation

HRID 1492011 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1/[CH:20]=[CH:21]/[C:22]([O:24][CH3:25])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.[Pd]>[Si:1]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86748310HCID 86748310, compound

Product 1

HCID 57126774HCID 57126774, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6.7 g (0.0184 mol) of methyl (E)-(2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-2-propenoate in 94 mL of ethanol is hydrogenated over 0.7 g of 10% palladium on carbon catalyst at atmospheric pressure. The catalyst is filtered, washed with ethanol and the filtrates are evaporated to dryness to give methyl (2S,3S,4S)-3-[4-(t-butyl-dimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]propanoate as an oil with elemental analysis: C, 62.77; H, 8.35: N, 3.84 (theory: C, 62.43: H, 8.55: N, 3.83).

Workup

  1. filtrationThe catalyst is filtered
  2. washwashed with ethanol
  3. customthe filtrates are evaporated to dryness

Sources & evidence

ORD record
ord-43cc4eb1c434453a84c6b856756dda1a
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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