(2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile → (2S,4S)-1-[[N-[4-(pyrrolidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 227941Notes

Reaction equation

HRID 227941 reaction equation
C(OC([N:11]([CH2:28][C:29]([N:31]1[CH2:35][C@@H:34]([F:36])[CH2:33][C@H:32]1[C:37]#[N:38])=[O:30])[C:12]12[CH2:19][CH2:18][C:15]([C:20]([N:22]3[CH2:27][CH2:26]C[CH2:24][CH2:23]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=O)C1C=CC=CC=1.[H][H]>C(O)C.ClCCl.[C].[Pd]>[N:22]1([C:20]([C:15]23[CH2:18][CH2:19][C:12]([NH:11][CH2:28][C:29]([N:31]4[CH2:35][C@@H:34]([F:36])[CH2:33][C@H:32]4[C:37]#[N:38])=[O:30])([CH2:13][CH2:14]2)[CH2:17][CH2:16]3)=[O:21])[CH2:23][CH2:24][CH2:26][CH2:27]1

Participants

6

Reactant 2

HCID 68844891(2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 57756697(2S,4S)-1-[[N-[4-(pyrrolidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileYield 70.6%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4S)-1-[[N-Benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (30.0 mg) and 10% palladium carbon (3.0 mg) were dissolved in ethanol (1.0 mL) and dichloromethane (0.5 mL). The mixture was stirred at room temperature for 8 hours in a hydrogen atmosphere. The mixture was then filtered through a Celite pad and the solvent was concentrated under reduced pressure. The resulting residue was purified by column chromatography (eluant:dichloromethane:methanol=10:1) to give (2S,4S)-1-[[N-[4-(pyrrolidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (15.2 mg).

Workup

  1. filtrationThe mixture was then filtered through a Celite pad
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customThe resulting residue was purified by column chromatography (eluant:dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-4b7e8c5ed27d4cf8a128c40c4ed58cc2
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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