(2R,5S)-2-(Acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester → (2S,5R)-5-(Acetylamino-methyl)-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

HRID 1527352Notes

Reaction equation

HRID 1527352 reaction equation
C(OC([N:11]1[C@H:15]([C:16](=[O:29])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=2)[CH2:14][CH2:13][C@@H:12]1[CH2:30][NH:31][C:32](=[O:34])[CH3:33])=O)C1C=CC=CC=1>C1COCC1.[Pd]>[F:27][C:25]([F:26])([F:28])[O:24][C:20]1[CH:19]=[C:18]([NH:17][C:16]([C@@H:15]2[CH2:14][CH2:13][C@H:12]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[NH:11]2)=[O:29])[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 68284355(2R,5S)-2-(Acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 71042618(2S,5R)-5-(Acetylamino-methyl)-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,5S)-2-(acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (48 mg, 0.1 mmol) in THF (0.3 mL) was added Pd/C (10%, 2.1 mg). The solution was degassed 3 times replacing air by nitrogen and finally nitrogen by hydrogen. The reaction mixture was further stirred under hydrogen atmosphere for 5 h. The catalyst was removed through a pad of Celite and washed with THF. Solvents were concentrated and the resulting residue was used without further purification in the next step. MS (LC/MS): 346 [M+H]+; tR (HPLC conditions b): 2.94 min.

Workup

  1. customThe solution was degassed 3 times
  2. customThe catalyst was removed through a pad of Celite
  3. washwashed with THF
  4. concentrationSolvents were concentrated
  5. customthe resulting residue was used without further purification in the next step
  6. custom2.94 min.

Sources & evidence

ORD record
ord-9a8387ceaf264c498ecb93035752e9bf
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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