Ethyl Acetate → HCID 22036275, compound

HRID 1789697Notes

Reaction equation

HRID 1789697 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:6][CH:5]=[CH:4][N:3]=1.[NH:18]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19]1.[H-].[Na+].CCOC(C)=O>O1CCOCC1>[NH:18]1[CH2:22][CH2:21][CH:20]([O:23][C:2]2[C:7]([O:8][CH2:9][CH2:10][O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:6][CH:5]=[CH:4][N:3]=2)[CH2:19]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 982104-HydroxypyrrolidineHCID 22036365HCID 22036365, compound

Product 1

HCID 22036275HCID 22036275, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-3-(2-phenoxyethoxy)pyrazine (150 mg, 0.60 mmol; from Example 1, Step 1) was added to a stirred mixture of 3-pyrrolidinol (260 mg, 2.99 mmol) and NaH (55% dispersion in mineral oil; 110 mg, 2.50 mmol) in dioxane (2 mL), and the reaction was stirred at room temperature for 2 h. EtOAc was added and the mixture was washed with water, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel using EtOAc/MeOH/HOAc/H2O (50:40:9:1) as eluent to give 38 mg (22%) of the title compound. Anal. (C16H19N3O3) H; C: calcd, 63.77; found, 62.20; N: calcd, 13.94; found, 13.0.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8ff57be5427f4569bde3cf527b709aa1
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

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