HCID 11292172, compound → HCID 12051141, compound

HRID 496042Notes

Reaction equation

HRID 496042 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:27][O:26][C:16]3[CH:17]=[CH:18][C:19]4[C:20](=O)[CH:21]=[CH:22][O:23][C:24]=4[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)(=O)C.[Pt]=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:27][O:26][C:16]3[CH:17]=[CH:18][C:19]4[CH2:20][CH2:21][CH2:22][O:23][C:24]=4[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 11292172HCID 11292172, compound

Product 1

HCID 12051141HCID 12051141, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

[(2R)-7-Oxo-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-2-yl]methyl 4-methylbenzenesulfonate (1.0 g, 2.6 mmole) dissolved in acetic acid (50 mL) was hydrogenated at 40 psi in the presence of 0.30 g platinum oxide on a Parr shaker for 5 hours. The catalyst was filtered through celite and the filter cake washed with water. The filtrate was then extracted with ethyl acetate and the organic layer was washed with saturated sodium bicarbonate until neutral. The organic extracts were dried over magnesium sulfate, filtered and evaporated to give 0.78 g (81%) of the (R)-enantiomer of the title compound as a clear oil. 1H (CDCl3) doublet 7.8 δ (2H); doublet 7.4 δ (2H); singlet 6.5 δ (1H); singlet 6.4 δ (1H); multiplet 4.2 δ (1H); multiplet 4.1-4.3 δ (5H); multiplet 4.0 δ (1H); triplet 2.7 δ (2H); singlet 2.4 δ (3H); triplet 2.0 δ (2H).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. washthe filter cake washed with water
  3. extractionThe filtrate was then extracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium bicarbonate until neutral
  5. dry with materialThe organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-732353e774be4de7a0e713215f05b424
Source dataset
uspto-grants-2005_09
Patent number
US06943178B2

Reaction notes

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