1,3-Bis(diphenylphosphino)propane → HCID 23021225, compound

HRID 2223874Notes

Reaction equation

HRID 2223874 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].N[CH:45]1[CH2:50][CH2:49][N:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH2:47][CH2:46]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([CH:45]2[CH2:50][CH2:49][N:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH2:47][CH2:46]2)=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 5642162-Bromo-5-methylpyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 23021225HCID 23021225, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-Bromo-5-methylpyridine (8.56 g), 1,3-bis(diphenylphosphino)propane (4.10 g) and sodium tert-butoxide (6.69 g) were suspended in toluene (500 mL), to which was added ethyl 4-amino-1-piperidinecarboxylate (10.28 g). Tris(dibenzylideneacetone)dipalladium (3.19 g) was added to the suspension, and it was stirred at 70° C. for 4 hours. Ethyl acetate was added to the reaction solution, and then, it was washed with saturated aqueous sodium chloride solution, and dried (MgSO4). The solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography (silica gel, ethyl acetate), and then crystallized (ethyl acetate/hexane) to give the title compound (10.13 g).

Workup

  1. washit was washed with saturated aqueous sodium chloride solution
  2. dry with materialdried (MgSO4)
  3. distillationThe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by chromatography (silica gel, ethyl acetate)
  5. customcrystallized (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ab7f1150c5b7406ebf97e2134875f90b
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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