Trifluoroacetic acid → HCID 11001175, compound

HRID 2104326Notes

Reaction equation

HRID 2104326 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@H:16]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]([N:19]1[CH2:24][CH2:23][CH2:22][C@@H:21]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:20]1)=[O:18])C)(C)(C)C>ClCCl>[CH3:27][N:26]([CH2:25][C@@H:21]1[CH2:22][CH2:23][CH2:24][N:19]([C:17](=[O:18])[C@H:16]([NH:14][CH3:13])[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:20]1)[CH3:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11025837HCID 11025837, compound

Product 1

HCID 11001175HCID 11001175, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., trifluoroacetic acid (25 ml) was added to a solution of N-[(1R)-1-benzyl-2-((3S)-3-(dimethylaminomethyl)piperidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (1.69 g, 4.2 mmol) in dichloromethane (25 ml). The reaction mixture was stirred for 30 min at 0° C. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (100 ml) and the solvent was removed in vacuo. The latter procedure was repeated two times. The crude product was purified by flash chromatography on silica (90 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 1.15 g of (2R)-1-((3S)-3-((dimethylamino)methyl)piperidin-1-yl)-2-methylamino-3-phenylpropan-1-one.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  3. customthe solvent was removed in vacuo
  4. customThe crude product was purified by flash chromatography on silica (90 g)

Sources & evidence

ORD record
ord-388849bdbd0d42439636d5cba3361b68
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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