(4S,5S)-5-((benzyloxy)methyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2(3H)-one → (4S,5S)-4-(1,3-dioxolan-2-yl)-5-(hydroxymethyl)dihydrofuran-2(3H)-one

HRID 896832Notes

Reaction equation

HRID 896832 reaction equation
C([O:8][CH2:9][C@H:10]1[O:14][C:13](=[O:15])[CH2:12][C@@H:11]1[CH:16]1[O:20][CH2:19][CH2:18][O:17]1)C1C=CC=CC=1>CO.[Pd]>[O:17]1[CH2:18][CH2:19][O:20][CH:16]1[C@@H:11]1[C@@H:10]([CH2:9][OH:8])[O:14][C:13](=[O:15])[CH2:12]1

Participants

4

Reactant 1

HCID 11150125(4S,5S)-5-((benzyloxy)methyl)-4-(1,3-dioxolan-2-yl)dihydrofuran-2(3H)-one

Product 1

HCID 11116788(4S,5S)-4-(1,3-dioxolan-2-yl)-5-(hydroxymethyl)dihydrofuran-2(3H)-oneYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of dihydrofuranone (14) (0.5 g, 1.79 mmol) in MeOH (30 mL) was added Pd/C (25 mg). The mixture was stirred at room temperature under an H2 balloon for 24 hours, and then filtered over Celite. Removal of solvent under reduced pressure, followed by column chromatography on silica gel (35% EtOAc in hexanes as the eluent) yielded the compound (15) (301 mg, 89%) as a white solid, Rf=0.28 (50% EtOAc in hexanes), [α]25D 22° (c 1.32, CHCl3); 1H-NMR (500 MHz, CDCl3) δ: 2.54 (dd, 1H, J=6.0, 11.4 Hz), 2.68-2.81 (m, 2H), 3.66 (dd, 1H, J=3.9-8.5 Hz), 3.88-3.95 (m, 3H), 3.97-4.02 (m, 2H), 4.53 (m, 1H), 4.91 (d, 1H, J=3.9 Hz); 13C-NMR (125.8 MHz, CDCl3) δ: 30.68, 40.12, 64.36, 65.77, 81.07, 103.94, 176.83.

Workup

  1. filtrationfiltered over Celite
  2. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-1d63b2e0f71b4d4297668395bd4377bf
Source dataset
uspto-grants-2005_07
Patent number
US06919465B2

Reaction notes

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