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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
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HRID 552903 반응식
[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
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참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)촉매HCID 1140
Toluene
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4de319d61a66409c8470a3c582602518
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951951B2

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