Reaction #531805

ord-cda1e91de3df47838ccda7975c2a3996

Reaction equation

CC(C)(C)OC(=O)NCCCC(CCCNC(=O)OC(C)(C)C)(CCCNC(=O)OC(C)(C)C)[N+](=O)[O-]
tris(3-(tert-butoxycarbonylamino)propyl)nitromethane
CC(C)(C)OC(=O)NCCCC(CCCNC(=O)OC(C)(C)C)(CCCNC(=O)OC(C)(C)C)[N+](=O)[O-]
Tris(3-(tertbutoxycarbonylamino)propyl)nitromethane
O=C(O)C(F)(F)F
trifluoroacetic acid
→
NCCCC(CCCN)(CCCN)[N+](=O)[O-].O=C(O)C(F)(F)F
title compound 10c
Yield 100.0%
NCCCC(CCCN)(CCCN)[N+](=O)[O-].O=C(O)C(F)(F)F
Tris(3-aminopropyl)nitromethane trifluoroacetate salt
Yield 100.0%

Reactants

CC(C)(C)OC(=O)NCCCC(CCCNC(=O)OC(C)(C)C)(CCCNC(=O)OC(C)(C)C)[N+](=O)[O-]
tris(3-(tert-butoxycarbonylamino)propyl)nitromethane
CC(C)(C)OC(=O)NCCCC(CCCNC(=O)OC(C)(C)C)(CCCNC(=O)OC(C)(C)C)[N+](=O)[O-]
Tris(3-(tertbutoxycarbonylamino)propyl)nitromethane
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagents

None

Solvents

ClCCl
dichloromethane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe reaction was then concentrated under high vacuum

Procedure

A mixture of tris(3-(tert-butoxycarbonylamino)propyl)nitromethane 1c (10 g, 18.8 mmol) in trifluoroacetic acid (20 ml) and dichloromethane (50 ml) was stirred at room temperature for 4 h. The reaction was then concentrated under high vacuum to afford the title compound 10c (10.8 g, 18.8 mmol. 100%) as a gum.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08475768B2uspto-grants-2013_07