Trifluoroacetic acid → Ethyl (2S)-2-methylpiperazine-1-carboxylate

HRID 1970538Notes

Reaction equation

HRID 1970538 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][C@@H:7]1[CH3:19])=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][C@@H:7]1[CH3:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66856048(S)-2-Methyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-ethyl ester

Product 1

HCID 45099580Ethyl (2S)-2-methylpiperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.05 g (S)-2-Methyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-ethyl ester in 15 ml dichloromethane was treated with 11.2 ml TFA and the resulting solution stirred for 12 h. The solvents were removed in vacuum and the crude hydrotrifluoroacetate transformed to the free amine by treatment with (Polystyrylmethyl)trimethylammonium bicarbonate in MeCN. Yield: 1.70 g.

Workup

  1. customThe solvents were removed in vacuum

Sources & evidence

ORD record
ord-c76b5e9e007c41d7acb3b01333ae059a
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

Loading…