Sulfuric Acid → HCID 86612015, compound

HRID 500440Notes

Reaction equation

HRID 500440 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 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 chromatography
  9. washeluting with 0-10% (v/v) ethyl acetate in heptane

Sources & evidence

ORD record
ord-d302eeb7597f415fa1e80b2f0fe6f01b
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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