HCID 57779833, compound → HCID 57779822, compound

HRID 552898Notes

Reaction equation

HRID 552898 reaction equation
[CH2:1]([CH:4]1[O:8][C:7](=[O:9])[CH:6]=[C:5]1[N:10]([CH2:19][CH:20]=[CH2:21])[CH2:11][C:12]1[CH:13]=[N:14][C:15]([Cl:18])=[CH:16][CH:17]=1)C=C>ClCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[Cl:18][C:15]1[N:14]=[CH:13][C:12]([CH2:11][N:10]2[CH2:19][CH:20]=[CH:21][CH2:1][CH:4]3[O:8][C:7](=[O:9])[CH:6]=[C:5]23)=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 57779833HCID 57779833, compound

Product 1

HCID 57779822HCID 57779822, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

40 mg (0.13 mmol) of 5-allyl-4-{allyl[(6-chloropyridin-3-yl)methyl]amino}furan-2(5H)-one (VI-1) are dissolved in 4 ml of dichloromethane, 11 mg (0.013 mmol) of the second generation Grubbs catalyst are added and the mixture is stirred at room temperature for 2 hours. Concentration under reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate gives 29 mg (80% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-4,5,8,8a-tetrahydro-2H-furo[3,2-b]azepin-2-one.

Workup

  1. concentrationConcentration
  2. customunder reduced pressure and purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-a40b5600ac454a4cb97914103b18487b
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

Loading…