HCID 68313441, compound → HCID 68313537, compound

HRID 2404379Notes

Reaction equation

HRID 2404379 reaction equation
[C:1]1([C@@H:7]2[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Rh]>[CH:1]1([C@@H:7]2[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 68313441HCID 68313441, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68313537HCID 68313537, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

A solution of (1S,3R)-3-phenylcyclopentanamine (second eluting diastereomer from Example 15B, 106 mg, 0.657 mmol) and 1,1,1-trifluoroethanol (20 mL) was added to 5% Rh/Al2O3 (42.4 mg) in a 50 mL pressure bottle. The reaction was heated for 16 hours under 30 psi hydrogen pressure and at 50° C. The mixture was filtered through a nylon membrane, washing with EtOH (50 mL). The solution was concentrated to provide the title compound (77 mg, 70%). MS (DCI) m/z 168 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. washwashing with EtOH (50 mL)
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-51b15e85ec6746dca2d7f6e7d34df562
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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