Sulfuric Acid → HCID 86612015, compound

HRID 644032Notes

Reaction equation

HRID 644032 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=O.N[N:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH2:12][C@H:11]1[CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.S(=O)(=O)(O)O>C(O)C>[CH:20]1([C@H:11]2[N:10]3[C:2]([C:1]([O:6][CH2:7][CH3:8])=[O:5])=[CH:4][C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([C:15]=43)[O:13][CH2:12]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 12041Ethyl pyruvateHCID 68676230HCID 68676230, compound

Product 1

HCID 86612015HCID 86612015, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl pyruvate (882 mg, 7.59 mmol) was added to a solution of (R)-4-amino-3-cyclohexyl-3,4-dihydro-2H-1,4-benzoxazine (1.47 g, 6.33 mmol) in ethanol (40 ml). The reaction mixture was stirred at room temperature for 15 min. To the reaction mixture, sulfuric acid (10% v/v in ethanol; 8.0 ml) was added. The reaction mixture was refluxed for 2 h. The mixture was cooled to room temperature and partitioned between ethyl acetate and sodium carbonate solution. The aqueous layer was extracted with ethyl acetate and the combined organic layers washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography eluting with 0-10% (v/v) ethyl acetate in heptane to afford ethyl (R)-3-cyclohexyl-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine-5-carboxylate (1.49 g, 4.76 mmol).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperatureThe mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and sodium carbonate solution
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layers washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography
  9. washeluting with 0-10% (v/v) ethyl acetate in heptane

Sources & evidence

ORD record
ord-f34845b306094985b423b7dcf9a37df9
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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