HCID 137330059, compound → HCID 137330058, compound

HRID 1527346Notes

Reaction equation

HRID 1527346 reaction equation
[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([C:18]([CH3:26])([CH3:25])[O:19][SiH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])[N:14]2CC2C=CC=CC=2)=[O:12])[CH:7]=[CH:8][CH:9]=1>C1COCC1.[Pd]>[F:35][C:2]([F:1])([F:34])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([C:18]([CH3:26])([CH3:25])[O:19][SiH2:20][C:21]([CH3:22])([CH3:24])[CH3:23])[NH:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 137330059HCID 137330059, compound

Product 1

HCID 137330058HCID 137330058, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-1-benzyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide (97 mg, 0.19 mmol) in THF (1 mL) was added Pd/C (10%, 20 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. Solvent was concentrated and the crude residue was purified by preparative HPLC (Waters SunFire C18-ODB 5 μm, 19×50, 5-100% CH3CN/H2O in 17 min, 100% CH3CN for 3 min, CH3CN and H2O containing 0.1% TFA, flow: 20 mL/min) to give the desired compound. MS (LC/MS): 419 [M+H]+; tR (HPLC conditions b): 5.28 min.

Workup

  1. customThe solution was degassed 3 times
  2. customThe catalyst was removed through a pad of Celite
  3. washwashed with THF
  4. concentrationSolvent was concentrated
  5. customthe crude residue was purified by preparative HPLC (Waters SunFire C18-ODB 5 μm, 19×50, 5-100% CH3CN/H2O in 17 min, 100% CH3CN for 3 min, CH3CN and H2O containing 0.1% TFA, flow: 20 mL/min)

Sources & evidence

ORD record
ord-eabb8627949a458ea9a69acc8b8d46ff
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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