tert-Butyl piperazine-1-carboxylate → (S)-1-Boc-4-(oxiran-2-ylmethyl)piperazine

HRID 2364705Notes

Reaction equation

HRID 2364705 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.Cl[CH2:15][C@@H:16]1[CH2:18][O:17]1>C(O)C>[O:17]1[CH2:18][C@@H:16]1[CH2:15][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

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 149428(+)-Epichlorohydrin

Product 1

HCID 10977626(S)-1-Boc-4-(oxiran-2-ylmethyl)piperazineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tert-butyl piperazine-1-carboxylate 7a (7.44 g, 40 mmol) and (S)-2-chloromethyl-oxirane (3.70 g, 40 mmol) were dissolved in 60 mL of ethanol. The reaction solution was stirred for 12 hours. The resulting solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound tert-butyl 4-[[(2S)-oxiran-2-yl]methyl]piperazine-1-carboxylate 20a (9.20 g, yield: 95.0%) as a white solid.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-82a0d23784844d8f9eee4f4ee52d0d3a
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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