Diisopropylethylamine → (1R)-1'-{[1-(2-Fluoro-4-pyridin-2-ylphenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

HRID 557834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557834
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=O)[CH2:10][CH2:9]2)=[C:4]([F:14])[CH:3]=1.CC1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.[NH:30]1[CH2:34][CH2:33][C@@:32]2([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[C:36](=[O:43])[O:35]2)[CH2:31]1.F[P-](F)(F)(F)(F)F.[N:51]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:55]2C=[CH:57][CH:58]=[CH:59][C:54]=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[F:14][C:4]1[CH:3]=[C:2]([C:55]2[CH:54]=[CH:59][CH:58]=[CH:57][N:51]=2)[CH:7]=[CH:6][C:5]=1[C:8]1([C:11]([N:30]2[CH2:34][CH2:33][C@@:32]3([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[C:36](=[O:43])[O:35]3)[CH2:31]2)=[O:13])[CH2:9][CH2:10]1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576855791-(4-Chloro-2-fluorophenyl)cyclopropane-1-carboxylic acidHCID 86602274[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid (1R)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Produkt 1

HCID 66661642(1R)-1'-{[1-(2-Fluoro-4-pyridin-2-ylphenyl)cyclopropyl]-carbonyl}-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-chloro-2-fluorophenyl)cyclopropanecarboxylic acid (0.15 g, 0.7 mmol), [(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid-(1R)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one (1:1) salt (0.29 g, 0.7 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.34 g, 0.77 mmol), and N,N-diisopropylethylamine (0.43 ml, 2.4 mmol) in N,N-dimethylformamide (2.0 ml) was stirred at room temperature overnight. The mixture then was diluted with ethyl acetate. The resulting solution was washed with saturated NaHCO3 solution, water, 1N HCl solution, water and brine successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated to afford the desired product (275 mg).

Aufarbeitung

  1. washThe resulting solution was washed with saturated NaHCO3 solution, water, 1N HCl solution, water and brine successively
  2. dry with materialthen dried over Na2SO4
  3. filtrationand then filtered
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-6a667d722ac2449aaac09aac5d4c5c97
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058288B2

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