Trifluoroacetic acid → (R)-2-Methyl-piperazine-1-carboxylic acid ethyl ester

HRID 1970525Notes

Reaction equation

HRID 1970525 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 66855072(R)-2-Methyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-ethyl ester

Product 1

HCID 45099581(R)-2-Methyl-piperazine-1-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.05 g (R)-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: 1.45 g.

Workup

  1. customThe solvents were removed in vacuum

Sources & evidence

ORD record
ord-24372b3a29414b84b6a443bbe2afbaf8
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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