HCID 68157732, compound → HCID 68157390, compound

HRID 242782Notes

Reaction equation

HRID 242782 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[C@@H:23]([NH:25]C(OCC2C=CC=CC=2)=O)[CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]=[C:15]2[C@@H:23]([NH2:25])[CH3:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 68157732HCID 68157732, compound

Product 1

HCID 68157390HCID 68157390, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

To a nitrogen purged solution of 4-[2-((S)-1-benzyloxycarbonylaminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester (308 mg, 0.644 mmol) in IMS (10 mL) was added 10% Pd/C (32 mg) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 2 h. Additional quantities of 10% Pd/C were subsequently added (41 mg after 2 h and 33 mg after 4 h) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 17 h. The suspension was filtered through a PTFE frit and washed with additional IMS. The filtrate was concentrated in vacuo affording 4-[2-((S)-1-Aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester as a pale yellow oil (202 mg). LCMS: RT 2.34 min [M+H]+ 345.2

Workup

  1. stirringthe reaction mixture was stirred at RT under a hydrogen atmosphere for 17 h
  2. filtrationThe suspension was filtered through a PTFE frit
  3. washwashed with additional IMS
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5f4ceb95a347465c85602f81212b7b61
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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