Water → (3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5,5-dioxide

HRID 2178199Notes

Reaction equation

HRID 2178199 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[C@@:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])([CH3:15])[C@@H:13]2[C@@H:9]([CH2:10][O:11][CH2:12]2)[O:8][S:7]1=[O:23].I([O-])(=O)(=O)=[O:31].[Na+].C(#N)C.O>C(OCC)(=O)C.[Ru](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[C@@:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])([CH3:15])[C@@H:13]2[C@@H:9]([CH2:10][O:11][CH2:12]2)[O:8][S:7]1(=[O:31])=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 23667635Sodium periodateHCID 70654406(3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5-oxide

Product 1

HCID 88876324(3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5,5-dioxideYield 55%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

A solution of (3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5-oxide (7.24 g, 17.2 mmol) and sodium periodate (4.04 g, 18.9 mmol) in a mixture of ethyl acetate (60 ml), acetonitrile (60 ml) and cold water (99.6 ml) was treated with ruthenium(III) chloride (35.6 mg, 172 μmol). The reaction mixture was stirred at 23° C. for 30 minutes. For the workup, the reaction mixture was extracted with a saturated solution of sodium hydrogencarbonate, the aqueous layer re-extracted with ethyl acetate, and the combined organic layers were dried over sodium sulphate and evaporated. The residue was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 0:100 as the eluent. The (3aS,7S,7aS)-rel-6-(2,4-dimethoxy-benzyl)-7-(2-fluoro-phenyl)-7-methyl-hexahydro-2,4-dioxa-5-thia-6-aza-indene 5,5-dioxide (4.1 g, 55% yield) was obtained as a light yellow solid. MS (ISP): m/z=460.2 [M+Na]+.

Workup

  1. extractionFor the workup, the reaction mixture was extracted with a saturated solution of sodium hydrogencarbonate
  2. extractionthe aqueous layer re-extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulphate
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 0:100 as the eluent

Sources & evidence

ORD record
ord-bbe1b0c67f1142fbb1f6300e9c50c834
Source dataset
uspto-grants-2015_06
Patent number
US09067924B2

Reaction notes

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