HCID 8030588, compound → HCID 10811759, compound

HRID 2092766Notes

Reaction equation

HRID 2092766 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[CH:9]=[CH:8][O:7][CH2:6]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[CH2:9][CH2:8][O:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 8030588HCID 8030588, compound

Product 1

HCID 10811759HCID 10811759, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (3R,4S)-3,4-dihydro-2H-pyran-3,4-diyl diacetate (8 g, 40 mmol) and Pd/C (10%, 5.0 g) in MeOH was stirred at RT for 12 h under H2 atmosphere (50 psi). After filtration, the residue was concentrated to give the title compound, which was used without further purification (7.5 g). 1H NMR (400 MHz, CDCl3) δ ppm 2.06 (s, 6H), 3.95-4.03 (m, 2H), 4.84 (t, J=4.0 Hz, 1H), 5.15-5.20 (m, 1H), 5.43 (t, J=4.0 Hz, 1H), 6.49 (d, J=4.0 Hz, 1H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe residue was concentrated

Sources & evidence

ORD record
ord-033043e02c344f95bca58d4a9ae960af
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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