Diazomethane → Ethyl 1-(1-benzyloxycarbonyl-3-(R)-pyrrolidinyl)cyclopropanecarboxylate

HRID 1457978Notes

Reaction equation

HRID 1457978 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([C:16](=[CH2:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH2:25])=[N-]>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([C:16]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:25][CH2:22]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 54203926HCID 54203926, compound

Product 1

HCID 54012988Ethyl 1-(1-benzyloxycarbonyl-3-(R)-pyrrolidinyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 852 mg (2.8 mmol) of ethyl 2-(1-benzyloxycarbonyl-3-(R)-pyrrolidinyl)acrylate and 5 mg (0.02 mmol) of palladium acetate was added 100 ml of diethyl ether, followed by dropwise addition of a solution of excess (10 equivalents) diazomethane in diethyl ether while ice cooling. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. After completion of the reaction, the solvent was evaporated and the resulting residue was applied to a silica gel column chromatography to yield 890 mg (quantitative) of the title compound as an oily substance from the eluate of n-hexane:ethyl acetate=3:1.

Workup

  1. additionAfter completion of the dropwise addition
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8d439d6c4d4c406bbfaf0836b3359585
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

Loading…