[(2R)-7-nitro-8-(2-oxoethyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl4-methylbenzenesulfonate → 2,3-Dihydro-7H-[1,4]dioxino[2,3-e]indol-2-ylmethyl4-methylbenzenesulfonate

HRID 495406Notes

Reaction equation

HRID 495406 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH2:26][CH:27]=O)=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pt]=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3=[C:19]4[C:20](=[CH:21][CH:22]=[C:16]3[O:15][CH2:14]2)[NH:23][CH:27]=[CH:26]4)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 86586527[(2R)-7-nitro-8-(2-oxoethyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl4-methylbenzenesulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 218920712,3-Dihydro-7H-[1,4]dioxino[2,3-e]indol-2-ylmethyl4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3.75 g (9.2 mmole) of [(2R)-7-nitro-8-(2-oxoethyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate and 3.0 g of platinum oxide in 50 mL of ethyl acetate was treated with 45 psi of hydrogen on a Parr hydrogenation apparatus for 6 hours. The mixture was then filtered through celite and concentrated in vacuum. The residue was column chromatographed on silica gel with first 10% hexane/methylene chloride, then 1% methanol/methylene chloride and finally 2% methanol/methylene chloride to give 1.50 g of the (R)-enantiomer of the title compound as a white solid one-quarter hydrate, m.p. 145° C.

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated in vacuum
  3. customchromatographed on silica gel with first 10% hexane/methylene chloride

Sources & evidence

ORD record
ord-aaa7afcd4ade4827b79c08313af0131d
Source dataset
uspto-grants-2005_09
Patent number
US06939877B2

Reaction notes

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