Dimethylformamide → HCID 59171048, compound

HRID 1446136Notes

Reaction equation

HRID 1446136 reaction equation
CN(C)C=O.[O:6]=[C:7]1[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:9][CH:8]1[C:22]([O:24][CH2:25][CH3:26])=[O:23].[H][H]>[Ru].ClCCl.C1C=CC=CC=1.C1C=CC=CC=1.Cl[Ru]Cl.Cl[Ru]Cl>[OH:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:9][C@@H:8]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 150432781-Benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59171048HCID 59171048, compound

Reagents, catalysts & solvents 3

HCID 23950RutheniumCatalystHCID 10962144Benzeneruthenium(II) Chloride DimerCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
99.5 °C

Procedure

90 mL of dehydrated N,N-dimethylformamide was added to 2.58 g of benzene ruthenium (II) chloride dimer (5.15 mmol) and 6.73 g of (S)-(−)-2,2,′-bis(diphenylphosphino)-1,1-binaphthyl (S-BINAP) (10.8 mmol). The mixture was stirred for 10 minutes in an oil bath at an external temperature of 97 to 102° C. in an argon atmosphere. Subsequently, the mixture was stood to be cooled at room temperature. Volatile materials were evaporated under reduced pressure in an oil bath at an external temperature of 50 to 60° C. to give a catalyst. 300 g of 1-benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate (1.03 mol) and 500 mL of dehydrated dichloromethane were placed in an autoclave and the ruthenium catalyst dissolved in 850 mL of dehydrated dichloromethane was added. The mixture was stirred for 6 hours under a hydrogen pressure of 5 MPa at an external temperature of 50 to 62° C. Hydrogen was released and the reaction mixture was concentrated under reduced pressure. This gave 320 g of the title compound as a green oil. This product was used in the subsequent step without further purification.

Workup

  1. temperatureto be cooled at room temperature
  2. customVolatile materials were evaporated under reduced pressure in an oil bath at an external temperature of 50 to 60° C.
  3. customto give a catalyst
  4. additionwas added
  5. stirringThe mixture was stirred for 6 hours under a hydrogen pressure of 5 MPa at an external temperature of 50 to 62° C
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. customThis product was used in the subsequent step without further purification

Sources & evidence

ORD record
ord-8faf0d5884e2429d85140ac5a93c5fd3
Source dataset
uspto-grants-2010_02
Patent number
US07667049B2

Reaction notes

Loading…