Acetic Acid → HCID 131731401, compound

HRID 1026648Notes

Reaction equation

HRID 1026648 reaction equation
[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][C@@:11]3([CH3:15])[C@H:7]([CH2:8][N:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O)(=[O:23])C.[O-2].[Ce+4].[O-2].Br([O-])(=O)=O.[Na+]>O.O1CCOCC1>[Cl:1][C:2]1[C:14]2[C:13](=[O:23])[CH2:12][C@@:11]3([CH3:15])[C@H:7]([CH2:8][N:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10219615Ceric oxideHCID 23668195Sodium BromateHCID 131731400HCID 131731400, compound

Product 1

HCID 131731401HCID 131731401, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

cis-Ethyl 6-chloro-3a-methyl-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (5.55 mmol, 1630 mg) was dissolved in water (33 ml), acetic acid (8.25 ml) and 1,4-dioxane (8.25 ml). Cerium(IV) oxide (1.276 mmol, 220 mg) and sodium bromate (5.55 mmol, 837 mg) were added and the reaction mixture was heated to 95° C. for 3 hours. The reaction mixture was cooled to rt, diluted with water (30 ml) and extracted with ether. The organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo to give to give a crude residue that was purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane) to give cis-ethyl 6-chloro-3a-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (673 mg), m/z=308.7 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with ether
  3. dry with materialThe organic extracts were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give
  7. customto give a crude residue that
  8. customwas purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5a98790d329e4aafbe81b68d837e4dbc
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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