Diisopropylethylamine → (S)-2-(2,2,2-Trifluoro-ethoxymethyl)-pyrrolidine

HRID 1774748Notes

Reaction equation

HRID 1774748 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][CH2:15][C:16]([F:19])([F:18])[F:17])C1C=CC=CC=1.CCN(C(C)C)C(C)C>CO.[Pd]>[F:19][C:16]([F:17])([F:18])[CH2:15][O:14][CH2:13][C@@H:9]1[CH2:10][CH2:11][CH2:12][NH:8]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 86679127(S)-1-Benzyl-2-(2,2,2-trifluoro-ethoxymethyl)-pyrrolidine

Product 1

HCID 86679128(S)-2-(2,2,2-Trifluoro-ethoxymethyl)-pyrrolidineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-1-benzyl-2-(2,2,2-trifluoroethoxymethyl)-pyrrolidine (0.5 g, 1.83 mmol) in MeOH (20 mL) was added Hunig's base (1.18 g, 9.15 mmol). The flask was purged three times with Ar and 10% Pd/C (0.487 g, 0.457 mmol) was added to the mixture. The flask was purged three times with hydrogen and the reaction mixture was stirred at room temperature for 1 h. The mixture was filtered through a pad of Celite, washed with MeOH (20 mL) and the resulting solution was concentrated in vacuo to give the title compound (0.250 g, 75%) as a colorless semi-solid. MS: 184.1 (M+H+).

Workup

  1. additionwas added to the mixture
  2. customThe flask was purged three times with hydrogen
  3. filtrationThe mixture was filtered through a pad of Celite
  4. washwashed with MeOH (20 mL)
  5. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-facb5167bebc409e855e9c6282f82c13
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

Loading…