Water → HCID 46785871, compound

HRID 529795Notes

Reaction equation

HRID 529795 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].O>CN(C=O)C.CCOC(C)=O>[CH3:26][O:25][C:23](=[O:24])[CH2:22][CH2:21][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 76934Methyl 3-bromopropanoateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 46785871HCID 46785871, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl piperazine-1-carboxylate (1 g, 5.37 mmol) in DMF (20 mL) was added Cs2CO3 (589 mg, 1.81 mmol) and methyl 3-bromopropanoate (744 mg, 4.46 mmol). The resulting mixture was stirred at room temperature overnight. Water (50 m) and EtOAc (50 mL) was added. Phases were separated. The aqueous phase was extracted with EtOAc (50 mL). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 3.5% MeOH in DCM. Collection of appropriate fractions and evaporation of solvent afforded tert-butyl 4-(3-methoxy-3-oxopropyl)piperazine-1-carboxylate (895 mg, 74%) as yellow oil. TLC: Rf=0.3; ethyl acetate/petroleum ether=1/2.

Workup

  1. customPhases were separated
  2. extractionThe aqueous phase was extracted with EtOAc (50 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography on silica gel eluting with 3.5% MeOH in DCM
  7. customCollection of appropriate fractions and evaporation of solvent

Sources & evidence

ORD record
ord-c539858dba094306a95b0b01f4d18570
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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