Binap, (A+-)- → HCID 68455920, compound

HRID 2354463Notes

Reaction equation

HRID 2354463 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[CH:7]=1.[C:17]([O:21][C:22]([N:24]1[CH2:29][C@@H:28]2[CH2:30][C@H:25]1[CH2:26][NH:27]2)=[O:23])([CH3:20])([CH3:19])[CH3:18].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>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].O.C1(C)C=CC=CC=1>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:6]1[CH:7]=[C:2]([N:27]2[CH2:26][C@@H:25]3[CH2:30][C@H:28]2[CH2:29][N:24]3[C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH:3]=[N:4][CH:5]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 22573906HCID 22573906, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 68455920HCID 68455920, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a sealed pressure tube under an argon atmosphere, 3-bromo-5-(3-methoxyphenoxy)pyridine (0.53 g, 1.9 mmol), (1S,4S)-N-(tert-butoxycarbonyl)-2,5-diazabicyclo [2.2.1]heptane (0.469 g, 2.25 mmol), tris (dibenzylideneacetone)dipalladium(0) (0.050 g, 0.056 mmol), racemic-2,2′bis(diphenylphosphino)-1,1′binaphthyl (0.070 g, 0.11 mmol), sodium tert-butoxide (0.74 g, 7.5 mmol) and toluene (20 mL) was stirred at 70° C. for 24 h. The reaction mixture was poured into water (15 mL) and extracted with diethyl ether (3×30 mL). The combined diethyl ether extracts were dried (MgSO4), filtered and concentrated to a light-brown oil (1.3 g). The material was purified by chromatography on silica gel with ethyl acetate to gain a light-yellow oil (0.62 g, 83%).

Workup

  1. extractionextracted with diethyl ether (3×30 mL)
  2. dry with materialThe combined diethyl ether extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to a light-brown oil (1.3 g)
  5. customThe material was purified by chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-2867f2c567f4474bab40066f03536078
Source dataset
uspto-grants-2010_07
Patent number
USRE041439E1

Reaction notes

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