Trifluoroacetic acid → 2-Methyl-2-(piperazin-1-yl)propan-1-ol

HRID 1945563Notes

Reaction equation

HRID 1945563 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:18][C:14]([N:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)([CH3:17])[CH2:15][OH:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 574203451,1-Dimethylethyl 4-(2-hydroxy-1,1-dimethylethyl)-1-piperazinecarboxylate

Product 1

HCID 120525542-Methyl-2-(piperazin-1-yl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-hydroxy-1,1-dimethylethyl)piperazine-1-carboxylic acid tert-butyl ester (110 mg, 0.43 mmol) in DCM (3 mL) was added TFA (1 mL) and the resulting mixture stirred for 3 h. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH/DCM and the product eluted with 2M NH3/MeOH affording the title compound as an off-white solid (62 mg, 91%). 1H NMR (CDCl3, 400 MHz): δ 3.32 (2 H, s), 2.90 (5 H, t, J=4.78 Hz), 2.38-2.13 (4 H, m), 1.03 (6 H, s)

Workup

  1. washwas washed with MeOH/DCM
  2. washthe product eluted with 2M NH3/MeOH affording the title compound as an off-white solid (62 mg, 91%)

Sources & evidence

ORD record
ord-071b432bb5c4418a9a28dea9cbaaafe4
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…