Tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylate → 1-Piperazinecarboxamide

HRID 54100

Reaction equation

HRID 54100 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH:10](C(NC(C)(C)C)=O)[CH2:9]1)=O)(C)(C)C.C(OC([NH:31][C@@H](CC1C=CC=CC=1)[C@@H]1OC1)=O)C1C=CC=CC=1>C(O)(C)C>[N:8]1([C:6]([NH2:31])=[O:5])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 4063013Tert-butyl 3-(tert-butylcarbamoyl)piperazine-1-carboxylateHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Product 1

HCID 2581921-Piperazinecarboxamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.395 g of 4-(tert.butoxycarbonyl)-N-tert.butyl-2-piperazinecarboxamide was dissolved in 50 ml of dry isopropanol and treated with 0.413 g of 3(S)-(benzyloxyformamido)-1,2(S)-epoxy-4-phenylbutane. The mixture was stirred at room temperature for 72 hours. The solvent was removed by evaporation to give a brown semi-solid material which was purified by flash chromatography on silica gel using 5% methanol in dichloromethane for the elution. There was obtained 0.234 g of 1-[3(S)-(benzyloxyformamido)-2(R)-hydroxy-4-phenylbutyl]-4-(tert.butoxycarbonyl)-N-tert.butyl-2(R or S)-piperazinecarboxamide as a mixture of diastereomers.

Workup

  1. customThe solvent was removed by evaporation
  2. customto give a brown semi-solid material which
  3. customwas purified by flash chromatography on silica gel using 5% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-c7b15625057f47b2ab0684bbedde28e0
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Linked notes

Loading…