Triphenylphosphine → (5R)-5-[(E)-2-[3-chloro-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

HRID 70631

반응식

HRID 70631 반응식
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:41][C:42]1[CH:43]=[C:44](/[C:49](/[C:57]2[CH:62]=[CH:61][C:60]([CH:63]3[CH2:65][CH2:64]3)=[C:59]([O:66][CH3:67])[N:58]=2)=[CH:50]\[C@@H:51]2[NH:55][C:54](=[O:56])[CH2:53][CH2:52]2)[CH:45]=[CH:46][C:47]=1O>C1(C)C=CC=CC=1.O1CCCC1>[Cl:41][C:42]1[CH:43]=[C:44](/[C:49](/[C:57]2[CH:62]=[CH:61][C:60]([CH:63]3[CH2:64][CH2:65]3)=[C:59]([O:66][CH3:67])[N:58]=2)=[CH:50]\[C@@H:51]2[NH:55][C:54](=[O:56])[CH2:53][CH2:52]2)[CH:45]=[CH:46][C:47]=1[O:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67398720(5R)-5-[(E)-2-(3-chloro-4-hydroxyphenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

생성물 1

HCID 67400214(5R)-5-[(E)-2-[3-chloro-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

Tetrahydro-4-pyranol (127 mg), a 2.2 M solution of diisopropyl azodicarboxylate in toluene (0.655 mL) and triphenylphosphine (326 mg) were added to a solution of (5R)-5-[(E)-2-(3-chloro-4-hydroxyphenyl)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (160 mg) in tetrahydrofuran (3 mL), and the mixture was stirred at room temperature for four hours. The reaction solution was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give (5R)-5-[(E)-2-[3-chloro-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a colorless amorphous (120 mg, 61%).

후처리

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

출처 및 근거

ORD 기록
ord-3e5420e059944cd28496c22459623ef9
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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