Reaction #73082

ord-3fd893af0d6544c4821cd0d1f8d7b325

Reaction equation

CC[C@H](C(=O)OC)N(c1nc(Cl)ncc1[N+](=O)[O-])C1CCCC1
Intermediate A
CC[C@H](C(=O)OC)N(c1nc(Cl)ncc1[N+](=O)[O-])C1CCCC1
(R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate
→
CC[C@H](C(=O)OC)N(c1nc(Cl)ncc1[N+](=O)[O-])C(C)C
(R)-methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(isopropyl)amino)butanoate

Reactants

CC[C@H](C(=O)OC)N(c1nc(Cl)ncc1[N+](=O)[O-])C1CCCC1
Intermediate A
CC[C@H](C(=O)OC)N(c1nc(Cl)ncc1[N+](=O)[O-])C1CCCC1
(R)-Methyl 2-((2-chloro-5-nitropyrimidin-4-yl)(cyclopentyl)amino)butanoate

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherIntermediate C-1 was prepared similarly to the synthetic methods

Procedure

Intermediate C-1 was prepared similarly to the synthetic methods used to prepare Intermediate A with the exception that acetone was used instead of cyclopentanone in the reductive amination step.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541418B2uspto-grants-2013_09