Triphenylphosphine → HCID 57779816, compound

HRID 552899Notes

Reaction equation

HRID 552899 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:15][CH:14]=[CH:13][CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 57779822HCID 57779822, compound

Product 1

HCID 57779816HCID 57779816, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 1140TolueneSolvent

Procedure

10 mg (0.036 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-4,5,8,8a-tetrahydro-2H-furo[3,2-b]azepin-2-one (1-6) are dissolved in 10 ml of toluene, 5 mg (0.005 mmol) of tris(triphenylphosphine)rhodium(I) chloride and 4 mg (0.015 mmol) of triphenylphosphine are added and the mixture is hydrogenated under a hydrogen pressure of 3 bar and at 110-120° C. for 24 hours. The mixture is filtered and the filtrate is concentrated under reduced pressure. 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 mixture ethyl acetate:cyclohexane (2:1 to 4:1) gives 8 mg (79% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-4,5,6,7,8,8a-hexahydro-2H-furo[3,2-b]azepin-2-one.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customPurification 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-677ac500b1ab47f5883f1792d82c1f4f
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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