Trifluoroacetic acid → HCID 11098231, compound

HRID 2104333Notes

Reaction equation

HRID 2104333 reaction equation
FC(F)(F)C(O)=O.C(O[C:13](=O)[N:14]([C@H:16]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][N:25]([CH3:27])[CH3:26])=[O:18])C)(C)(C)C>ClCCl>[CH3:26][N:25]([CH2:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:17](=[O:18])[C@H:16]([NH:14][CH3:13])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10992766HCID 10992766, compound

Product 1

HCID 11098231HCID 11098231, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., trifluoroacetic acid (8 ml) was added to a solution of N-[(1R)-1-benzyl-2-((2S)-2-((dimethylamino)methyl)pyrrolidin-1-yl)-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (2.26 g, 5.80 mmol) in dichloromethane (8 ml). The reaction mixture was stirred for 20 min at 0° C. The solvent was removed in vacuo. Dichloromethane (70 ml) was added, 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 1.24 g of (2R)-1-((2S)-2-((dimethylamino)methyl)pyrrolidin-1-yl)-2-methylamino-3-phenylpropan-1-one.

Workup

  1. customThe solvent was removed in vacuo
  2. additionDichloromethane (70 ml) was added
  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-a660cb0ed0f14761892084d9ab4e306f
Source dataset
uspto-grants-2009_08
Patent number
US07576062B2

Reaction notes

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