Ethyl Acetate → HCID 68541607, compound

HRID 1993640Notes

Reaction equation

HRID 1993640 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]([N:19]1[CH2:24][C@@H:23]([CH3:25])[NH:22][CH2:21][C@@H:20]1[CH3:26])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[C:15]([O:14][C:12]([N:19]1[CH2:24][C@@H:23]([CH3:25])[N:22]([C:2]2[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=2)[CH2:21][C@@H:20]1[CH3:26])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 896482-Chloro-3-methyl-5-nitropyridineHCID 11745988(2S,5R)-1-Boc-2,5-dimethylpiperazine

Product 1

HCID 68541607HCID 68541607, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve 2-chloro-3-methyl-5-nitropyridine (310 mg, 1.82 mmol, 1.0 equiv) and N—BOC-trans-2,5-dimethylpiperazine (397 mg, 2.0 mmol, 1.1 equiv) in 5 mL of anhydrous DMF, add potassium carbonate (251 mg, 1.82 mmol, 1.0 equiv) and stir the mixture for 20 hours at 80° C. Pour the solution in a 1:1 v/v mixture of EtOAc and iced water. Extract the aqueous phase with EtOAc (2×20 mL) and wash the combined organic layers with water (3×20 mL) and saturated aq. sodium chloride (30 mL). Dry the organic solution over sodium sulfate and concentrate under reduced pressure to obtained a crude rac-(trans)-2,5-dimethyl-4-(3-methyl-5-nitro-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester. MS(ES+): m/z=251.2 (M+H).

Workup

  1. additionPour the solution
  2. extractionExtract the aqueous phase with EtOAc (2×20 mL)
  3. washwash the combined organic layers with water (3×20 mL) and saturated aq. sodium chloride (30 mL)
  4. dry with materialDry the organic solution over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-b96dc4a026ed452983cb017f24e615fe
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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