HCID 54173577, compound → HCID 54354626, compound

HRID 850618Notes

Reaction equation

HRID 850618 reaction equation
[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH:6]([N:17](CC1C=CC=CC=1)[C@@H](C1C=CC=CC=1)C)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[C:9]([F:16])[CH:8]=1)[CH3:2]>CCO.CC(O)=O.[OH-].[OH-].[Pd+2]>[CH2:1]([O:3][C:4](=[O:33])[CH2:5][CH:6]([NH2:17])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[C:9]([F:16])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 54173577HCID 54173577, compound

Product 1

HCID 54354626HCID 54354626, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of the dibenzylamine 14-4 (30.0 gm, 66.8 mmol) in EtOH/HOAc (340/30 mL) was purged with argon and treated with Pd(OH)2 (6 g) and placed under 1 atm of H2 for 12 h. Additional portions (2.5 g) of Pd(OH)2 were added after 24 h and 48 h. The reaction mixture was purged with argon, filtered through Celite, and the filtrate collected. The filtrate was concentrated to yield the desired amine 14-5.

Workup

  1. customThe reaction mixture was purged with argon
  2. filtrationfiltered through Celite
  3. customthe filtrate collected
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dc68d7f66374454aa99564ef16b637df
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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