HCID 18637143, compound → HCID 18637152, compound

HRID 329510Notes

Reaction equation

HRID 329510 reaction equation
C([O:8][CH2:9][C@H:10]1[C@H:15]([O:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH2:14][CH2:13][CH2:12][O:11]1)C1C=CC=CC=1.[H][H]>O1CCCC1.[Pd]>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][C@@H:15]1[CH2:14][CH2:13][CH2:12][O:11][C@H:10]1[CH2:9][OH:8]

Participants

5

Reactant 2

HCID 18637143HCID 18637143, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18637152HCID 18637152, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.93 g of dl-trans-2-benzyloxymethyl-3-(tetrahydropyran-2-yloxy)tetrahydropyran (prepared as described in Preparation 35) were dissolved in 130 ml of tetrahydrofuran and were then hydrogenated at room temperature for 8 hours in the presence of 1.30 g of a 10% w/w palladium on activated carbon catalyst and of hydrogen at an initial pressure of 4 atmospheres (about 4 bars). The catalyst was removed by filtration, and then the solvent was distilled off. The resulting residue was purified by column chromatography through 50 g of silica gel. Those fractions eluted with mixtures of hexane and diethyl ether ranging from 2:1 to 1:1 by volume were worked up to give 1.87 g of the title compound as a colorless oil.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off
  3. customThe resulting residue was purified by column chromatography through 50 g of silica gel
  4. washThose fractions eluted with mixtures of hexane and diethyl ether ranging from 2:1 to 1:1 by volume

Sources & evidence

ORD record
ord-bb9492727c984e8d8f2a9cf733c6576b
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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