4-Methylmorpholine → 1,4-Bis(tert-butoxycarbonyl)-2-formylmethylpiperazine

HRID 352831Notes

Reaction equation

HRID 352831 reaction equation
CN1CCOCC1.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]1[CH2:28][CH2:29][OH:30])=[O:14])([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH:16]1[CH2:28][CH:29]=[O:30])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 79724-MethylmorpholineHCID 22710988di-tert-Butyl 2-(2-hydroxyethyl)piperazine-1,4-dicarboxylate

Product 1

HCID 227100181,4-Bis(tert-butoxycarbonyl)-2-formylmethylpiperazine

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (150 ml) was dissolved 1,4-bis(tert-butoxycarbonyl)-2-(2-hydroxyethyl)piperazine. Under ice cooling, N-methylmorpholine (2.14 g) and tetra-n-propylammonium perruthenate (0.97 g) were added to the reaction mixture, followed by stirring at room temperature for 17 hours. The reaction mixture was then distilled off under reduced pressure. The residue was subjected to chromatography on a silica gel column (hexane:ethyl acetate=9:1 to 2:1), whereby the title compound (3.11 g) was obtained as colorless powder.

Workup

  1. distillationThe reaction mixture was then distilled off under reduced pressure
  2. customwas obtained as colorless powder

Sources & evidence

ORD record
ord-e4e084b2d70246b787df9f9be46e0e48
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…