Ethyl diazoacetate → HCID 57517486, compound

HRID 2368089Notes

Reaction equation

HRID 2368089 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+](=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N-]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetate2×HCID 3304481-(Diphenylmethyl)azetidin-3-ol

Product 1

HCID 57517486HCID 57517486, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-(diphenylmethyl)azetidin-3-ol (12 g) and rhodium(II) acetate dimer (1.1 g) in toluene (150 mL) was added dropwise ethyl diazoacetate (6.28 g) at 80° C. The mixture was stirred at 80° C. for 3 hr. Furthermore, ethyl diazoacetate (6.28 g) was added dropwise at 80° C., and the mixture was stirred at 80° C. for 3 hr. The mixture was allowed to cool, and filtered through a silica gel short column. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (9.0 g).

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 hr
  2. temperatureto cool
  3. filtrationfiltered through a silica gel short column
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-36bdc063a403449e86e08a5229a0c7a9
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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