tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-[[(2R)-oxiran-2-yl]methyl]piperazine-1-carboxylate

HRID 2364686Notes

Reaction equation

HRID 2364686 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 2734062(-)-Epichlorohydrin

Product 1

HCID 11010131Tert-butyl 4-[[(2R)-oxiran-2-yl]methyl]piperazine-1-carboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tert-butyl piperazine-1-carboxylate 7a (3.72 g, 20 mmol) was dissolved in 40 mL of ethanol followed by the addition of (R)-2-chloromethyl-oxirane (1.85 g, 20 mmol). The reaction solution was stirred for 5 hours and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound tert-butyl 4-[[(2R)-oxiran-2-yl]methyl]piperazine-1-carboxylate 7b (3.55 g, yield: 74.0%) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-7ef6743e6cd14c99a129e5c779268a2d
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

Loading…