1,3-Bis(diphenylphosphino)propane → HCID 66798910, compound

HRID 1193255Notes

Reaction equation

HRID 1193255 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@H:8]2[N:11]([CH2:19][CH3:20])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:14]([O:13][C:12]([N:11]([CH2:19][CH3:20])[C@H:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:12]([O:13][CH3:14])=[O:18])[CH:10]=2)[CH2:6][CH2:7]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 66805281HCID 66805281, compound

Product 1

HCID 66798910HCID 66798910, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

(R)-tert-Butyl 6-bromo-2,3-dihydro-1H-inden-1-yl(ethyl)carbamate (15 g, 44.12 mmol, 1 eq) was dissolved in MeOH (180 ml) and DMSO (30 ml). The mixture was degassed for 30 minutes with argon, and then Pd(OAc)2 (0.513 g, 2.21 mmol, 0.05 eq), 1,3-bis(diphenyl-phosphino)propane (0.911 g, 2.21 mmol, 0.05 eq) and TEA (18.4 ml, 132.35 mmol, 3 eq) were added. The reaction mixture was stirred for 16 hours at 80° C. in an autoclave under CO pressure (80 psi) and then concentrated under reduced pressure. The residue was taken up in water (200 ml) and extracted with ethyl acetate (2×400 ml). The combined org. phases were washed with sat. NaCl solution (500 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 8% ethyl acetate in hexane). Yield: 77% (10.84 g, 33.97 mmol)

Workup

  1. customThe mixture was degassed for 30 minutes with argon
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with ethyl acetate (2×400 ml)
  4. washphases were washed with sat. NaCl solution (500 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by column chromatography (silica gel, 8% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-95d0cd0469014b8ca6116a3e44ef75cd
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

Loading…