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Triphenylphosphine → 4-[(6-chloropyridin-3-yl)methyl]-6-methyl-5,6,7,7a-tetrahydrofuro-[3,2-b]pyridin-2(4H)-one

HRID 552903
Notes
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Reaction equation

HRID 552903 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][C:13](=[CH2:15])[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[CH2:14][CH:13]([CH3:15])[CH2:12][CH:11]3[O:16][C:17](=[O:19])[CH:18]=[C:10]23)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 577798304-[(6-chloropyridin-3-yl)methyl]-6-methylene-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

Product 1

HCID 577798314-[(6-chloropyridin-3-yl)methyl]-6-methyl-5,6,7,7a-tetrahydrofuro-[3,2-b]pyridin-2(4H)-one

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst
HCID 1140
Toluene
Solvent

Procedure

150.0 mg (0.54 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-6-methylene-5,6,7,7a-tetrahydrofuro-[3,2-b]pyridin-2(4H)-one (cf. I-5) are dissolved in 75 ml of toluene, 40 mg (0.043 mmol) of tris(triphenylphosphine)rhodium(I) chloride and 15 mg (0.057 mmol) of triphenylphosphine are added and the mixture is hydrogenated under a hydrogen pressure of 3 bar and at 110-120° C. for 10 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 ethyl acetate/cyclohexane (2:1 to 4:1) gives both possible diastereomers of 4-[(6-chloropyridin-3-yl)methyl]-6-methyl-5,6,7,7a-tetrahydrofuro-[3,2-b]pyridin-2(4H)-one: (a) 85 mg (56% of theory) of diastereomer A and (b) after preparative HPLC 18 mg (12% of theory) of diastereomer B.

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-4de319d61a66409c8470a3c582602518
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07951951B2

Reaction notes

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