tert-Butyl piperazine-1-carboxylate → HCID 57597092, compound

HRID 2093432Notes

Reaction equation

HRID 2093432 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.[F:14][C:15]1[CH:26]=[CH:25][C:18]([CH2:19]OS(C)(=O)=O)=[CH:17][C:16]=1[N+:27]([O-:29])=[O:28]>CCOC(C)=O>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([CH2:19][C:18]2[CH:25]=[CH:26][C:15]([F:14])=[C:16]([N+:27]([O-:29])=[O:28])[CH:17]=2)[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 20026654HCID 20026654, compound2×

Product 1

HCID 57597092HCID 57597092, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 1.0 eq of methanesulfonic acid 4-fluoro-3-nitro-benzyl ester (2B) in DMF (about 0.6 M 2B in DMF) was added about 1.05 eq of TEA and about 1.0 eq of t-butyl piperazine-1-carboxylate. The mixture was stirred for 30 min at room temperature, diluted with EtOAc, washed with NH4Cl solution, dried (Na2SO4) and evaporated. Purification by flash chromatography over silica with 50% EtOAc/hexanes as the eluant afforded 4-(4-fluoro-3-nitro-benzyl)-piperazine-1-carboxylic acid tert-butyl ester (2C).

Workup

  1. washwashed with NH4Cl solution
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customPurification by flash chromatography over silica with 50% EtOAc/hexanes as the eluant

Sources & evidence

ORD record
ord-f430ebf12d9a406c879ec3d652217ddd
Source dataset
uspto-grants-2013_05
Patent number
US08445495B2

Reaction notes

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