Tetrahydrofuran → methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate

HRID 1473188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473188
[CH2:1]([N:8]1[C:12]2[C:13](=[O:30])[N:14]([CH3:29])[C:15]([CH2:24][C:25]([O:27][CH3:28])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[O:41]1CCCC1>>[CH2:1]([N:8]1[C:12]2[C:13](=[O:30])[N:14]([CH3:29])[C:15]([CH:24]([OH:41])[C:25]([O:27][CH3:28])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 3

HCID 8028Tetrahydrofuran2×HCID 2733832Lithium HexamethyldisilazideHCID 89462962methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

Produkt 1

HCID 89462710methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetateAusbeute 82 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate (2.3 g, 5.46 mmol) in Tetrahydrofuran (THF) (30 mL) was treated with LiHMDS (8.45 mL, 8.45 mmol) at −78° C. and then stirred for 1 hour. A solution of (2R,8aS)-(+)-(Camphorsulfonyl)oxaziridine (2.421 g, 10.56 mmol) in Tetrahydrofuran (THF) (20 mL) was added, the mixture was warmed to 0° C. and then stirred for 20 minutes. The mixture was quenched with HCl (1M) and then extracted with Ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified on silica gel (0-100% ethyl acetate/hexanes) to afford methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate (3.3 g, 4.53 mmol, 82% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.28 (s, 9H) 7.01-7.07 (m, 1H) 5.93-5.99 (m, 1H) 5.85-5.92 (m, 1H) 5.77-5.84 (m, 1H) 5.20-5.27 (m, 1H) 3.79 (s, 3H) 3.58 (s, 3H); LCMS (m/z) ES+=437 (M+1).

Aufarbeitung

  1. stirringstirred for 20 minutes
  2. customThe mixture was quenched with HCl (1M)
  3. extractionextracted with Ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel (0-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dbb1b038c0a241b1ac4bd93f2eac22c2
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012642B2

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