Diiodomethane → HCID 89666888, compound

HRID 2171273Notes

Reaction equation

HRID 2171273 reaction equation
ICI.[CH2:4]([N:11]([C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:30])[C@@H:12]1[C@H:17]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]2=[O:28])[CH2:16][CH:15]=[CH:14][CH2:13]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:37]([Zn]CC)C.C(=O)([O-])O.[Na+]>CO.C(Cl)Cl>[CH2:4]([N:11]([C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:30])[C@H:12]1[CH2:13][CH:14]2[CH:15]([CH2:37]2)[CH2:16][C@H:17]1[N:18]1[C:19](=[O:28])[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]1=[O:27])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 516892Sodium BicarbonateHCID 89666886HCID 89666886, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 89666888HCID 89666888, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent3×

Procedure

A methylene chloride (3 ml) solution containing diiodomethane (0.2 ml) and a methylene chloride solution (3 ml) containing 2-((1R,6S)-6-(benzyl ((R)-1-phenylethyl)amino)-3-cyclohexen-1-yl)isoindolin-1,3-dione (0.36 g) obtained in the 1st step were added to a methylene chloride solution (10 ml) containing diethyl zinc (1M in hexane) (2.47 ml), followed by stirring for 15 hours. Methanol and sodium hydrogen carbonate were added to the reaction solution. The reaction solution was filtered through Celite. The filtrate was extracted with ethyl acetate. The organic layers were washed with water and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:0.2). A 2-((3R,4S)-4-(benzyl ((R)-1-phenylethyl)amino)bicyclo[4.1.0]heptan-3-yl)isoindolin-1,3-dione (0.20 g) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. filtrationThe reaction solution was filtered through Celite
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe organic layers were washed with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:0.2)

Sources & evidence

ORD record
ord-8cb9b2964ce7449b827a7327f5a81802
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…