HCID 70359873, compound → HCID 14621461, compound

HRID 1651665Notes

Reaction equation

HRID 1651665 reaction equation
[O:1]([CH2:9][C@H:10]1[C:15](=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][O:13][C@@H:12]([CH3:22])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]>C(O)C.[Pd]>[O:1]([CH2:9][C@H:10]1[C@@H:15]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][O:13][C@@H:12]([CH3:22])[O:11]1)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 70359873HCID 70359873, compound

Product 1

HCID 14621461HCID 14621461, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (2R,4R)-4-t-butyldimethylsiloxymethyl -5-ethoxycarbonylmethylene-2-methyl-1,3-dioxane (17.0 g) in ethanol (170 ml) was shaken under hydrogen (3 atm) with 10% palladium on carbon at room temperature for 1.5 hours. After removal of the catalyst by filtration, the solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column (500 g) with a mixture of n-hexane and ethyl acetate (20:1) as an eluent to give (2R,4R,5S)-4-t-butyldimethylsiloxymethyl-5 -ethoxycarbonylmethyl-2-methyl-1,3-dioxane (9.52 g) as a pale yellow oil.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was chromatographed on a silica gel column (500 g) with a mixture of n-hexane and ethyl acetate (20:1) as an eluent

Sources & evidence

ORD record
ord-197c41a15eb64b219fe54500e3552648
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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