Ethyl Acetate → HCID 59134376, compound

HRID 1993471Notes

Reaction equation

HRID 1993471 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH3:6])[CH2:2]1.[NH2:7][C@H:8]1[C:21]2[C:12](=[CH:13][C:14]3[C:15]([CH3:23])=[CH:16][C:17]([Cl:22])=[N:18][C:19]=3[CH:20]=2)[O:11][C:10]([CH3:25])([CH3:24])[C@@H:9]1[OH:26].Cl([O-])(=O)(=O)=O.[Li+].C(OCC)(=O)C>O1CCOCC1>[Cl:22][C:17]1[CH:16]=[C:15]([CH3:23])[C:14]2[CH:13]=[C:12]3[O:11][C:10]([CH3:24])([CH3:25])[C@H:9]([OH:26])[C@@H:8]([NH:7][CH2:2][CH:3]([OH:1])[CH2:4][CH2:5][CH3:6])[C:21]3=[CH:20][C:19]=2[N:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 13853Oxirane, 2-propyl-HCID 23665649Lithium perchlorateHCID 59134312HCID 59134312, compound

Product 1

HCID 59134376HCID 59134376, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Under nitrogen stream, 1,2-epoxypentane (71 μL, 0.682 mmol) was added to a solution of (3R*,4S*)-4-amino-7-chloro-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinolin-3-ol (100 mg, 0.343 mmol) and lithium perchlorate (36 mg, 0.343 mmol) in dioxane (0.50 mL) at room temperature, and the resulting mixture was stirred at 70° C. for 25 hours. Upon the completion of the reaction, ethyl acetate was added thereto, the resulting reaction solution was washed with saturated aqueous sodium hydrogencarbonate solution and then with saturated aqueous sodium chloride solution, and then dried over magnesium sulfate and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/1) to obtain the aimed product (yield: 59%).

Workup

  1. additionwas added
  2. customthe resulting reaction solution
  3. washwas washed with saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialwith saturated aqueous sodium chloride solution, and then dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-17851e795a354f40a59d3a8e86a9feeb
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

Loading…