HCID 22940645, compound → Ammonia

HRID 1458957Notes

Reaction equation

HRID 1458957 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C@H:10]([CH2:26][CH2:27][C:28]#[N:29])[C:11](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:12])[CH:5]=[CH:4][N:3]=1>CC(O)C.N.[Rh]>[NH3:1].[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C@@H:10]2[CH2:26][CH2:27][CH2:28][NH:29][C:11]2=[O:12])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 1

HCID 22940645HCID 22940645, compound

Product 2

HCID 222AmmoniaYield 30%HCID 54567185HCID 54567185, compound

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 222AmmoniaSolventHCID 3776IsopropanolSolvent

Procedure

Nitrile 10-3 (9.48 g, 24.2 mmol) was dissolved in 200 mL i-PrOH sat. with NH3.5% Rh on alumina (10.69 g) was added, and the mixture was hydrogenated on a Parr shaker at 50 psi H2 pressure. After 3 d, the reaction mixture was filtered through Celite, re-saturated with NH3, treated with fresh 5% Rh on alumina (3.00 g), and hydrogenated at 50 psi for 1 d more. After filtering through Celite, the mixture was concentrated and purified by flash chromatography (silica, CH2Cl2, then 10%, 20%, then 30% NH3 sat. EtOH/CH2Cl2) to provide the lactam 10-4 as a crystalline yellow solid.

Workup

  1. filtrationthe reaction mixture was filtered through Celite, re-saturated with NH3
  2. additiontreated with fresh 5% Rh on alumina (3.00 g)
  3. waithydrogenated at 50 psi for 1 d more
  4. filtrationAfter filtering through Celite
  5. concentrationthe mixture was concentrated
  6. custompurified by flash chromatography (silica, CH2Cl2

Sources & evidence

ORD record
ord-cfdd0f14a0de45f6afbfb172c54d5f8b
Source dataset
uspto-grants-1998_12
Patent number
US05852045

Reaction notes

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