(2S,5R)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide → (2S,5R)-5-Hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

HRID 1527343Notes

Reaction equation

HRID 1527343 reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[N:14]2CC2C=CC=CC=2)=[O:12])[CH:7]=[CH:8][CH:9]=1>C1COCC1.CO.[Pd]>[F:27][C:2]([F:1])([F:28])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[NH:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 71042580(2S,5R)-1-Benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

Product 1

HCID 71042622(2S,5R)-5-Hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-1-benzyl-5-hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide (500 mg, 1.27 mmol) in THF (5 mL) containing 5 drops of MeOH was added Pd/C (10%, 27 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 overnight. The catalyst was removed through a pad of Celite and washed with THF. Solvents were concentrated and the resulting material was used without purification in the next step. MS (LC/MS): 305 [M+H]+; tR (HPLC conditions b): 2.89 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 material was used without purification in the next step
  6. custom2.89 min.

Sources & evidence

ORD record
ord-08c6163e2670493bb9933826ed0c30d6
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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