HCID 67490889, compound → [(1S,6R)-7-Oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid tert-butyl ester

HRID 1917379Notes

Reaction equation

HRID 1917379 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:25]C=C)[C@@H:12]([CH2:13][CH:14]=[CH2:15])[C:11](=[O:16])[N:10]([C@@H:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCl>[C:1]([O:5][C:6]([C@:8]12[CH2:9][N:10]([C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[C:11](=[O:16])[C@@H:12]1[CH2:13][CH:14]=[CH:15][CH2:25]2)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 67490889HCID 67490889, compound

Product 1

HCID 67490838[(1S,6R)-7-Oxo-8-[(1R)-1-phenylethyl]-8-azabicyclo[4.3.0]non-3-en-1-yl]carboxylic acid tert-butyl esterYield 87.2%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The Second Generation Grubbs' catalyst (91.9 mg, 0.108 mmol) was added to a solution of (3S,4R)-3,4-diallyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (2.00 g, 5.41 mmol) in dichloromethane (54.1 mL) in a nitrogen atmosphere, and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→80:20→75:25→66:34→50:50) to give 1.61 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→90:10→80:20→75:25→66:34→50:50)

Sources & evidence

ORD record
ord-9fb8dc3714d64524b7caa0c4802122dd
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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