HCID 86586529, compound → HCID 22989532, compound

HRID 1168712Notes

Reaction equation

HRID 1168712 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C@H:10]([CH2:13][O:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[O:9][C:8]=2[C:25]=1[CH:26]=[C:27]([N+]([O-])=O)[CH2:28][CH3:29])([O-])=O.[H][H]>C(OCC)(=O)C.[Pt]=O>[CH3:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([O:14][CH2:13][CH:10]2[O:9][C:8]3=[C:25]4[C:4](=[CH:5][CH:6]=[C:7]3[O:12][CH2:11]2)[NH:1][C:27]([CH2:28][CH3:29])=[CH:26]4)(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 86586529HCID 86586529, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22989532HCID 22989532, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.70 g (1.5 mmole) of toluene-4-sulfonic acid (2R)-7-nitro-8-(2-nitro-but-1-enyl)-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester was dissolved in 100 mL of ethyl acetate and 0.10 g of platinum oxide added. The mixture was treated with 45 psi of hydrogen on a Parr hydrogenation apparatus for 5 hours. The mixture was then filtered through celite and concentrated in vacuum. The residue was column chromatographed on silica gel with 1:1 ethyl acetate/hexane to give 0.52 g of the (R)-enantiomer of the title compound as a yellow oil. 1H-NMR (CDCl3): doublet 7.8 δ (2H); doublet 7.3 δ (2H); doublet 6.76 δ (1H); doublet 6.64 δ (1H); singlet 6.16 δ (1H); multiplet 4.5 δ (1H); multiplet 4.3 δ (3H); quartet 4.1 δ (1H); quartet 2.75 δ (2H); singlet 2.5 δ (3H); triplet 1.3 δ (3H).

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated in vacuum
  3. customchromatographed on silica gel with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-fb161a93c35e4105ab38b69893492c43
Source dataset
uspto-grants-2003_09
Patent number
US06627639B2

Reaction notes

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