methyl 3-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-phenylmethoxy-benzoate → methyl 3-hydroxy-5-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate

HRID 600538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600538
[CH3:1][N:2]1[CH2:6][CH2:5][C@@H:4]([O:7][C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:18]CC3C=CC=CC=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[C:3]1=[O:26]>[Pd].C1COCC1.CO>[OH:18][C:16]1[CH:15]=[C:10]([CH:9]=[C:8]([O:7][C@@H:4]2[CH2:5][CH2:6][N:2]([CH3:1])[C:3]2=[O:26])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]

Komponenten

5

Edukt 1

HCID 59761149methyl 3-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-phenylmethoxy-benzoate2×

Produkt 1

HCID 59761141methyl 3-hydroxy-5-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of methyl 3-[(3R)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-5-phenylmethoxy-benzoate (Intermediate 13) (1.42 g, 4.0 mmol) was added to a suspension of 10% palladium on carbon (140 mg, catalytic) in THF (40 mL) and methanol (40 mL). The mixture was stirred under an atmosphere of hydrogen for 16 hours. The mixture was filtered and the filtrate evaporated under reduced pressure to give the product (1.04 g, 98%). 1H NMR δ (300 MHz, CDCl3) 2.06-2.20 (m, 1H), 2.56-2.68 (m, 1H), 2.97 (s, 3H), 3.37-3.55 (m, 2H), 3.86 (s, 3H), 4.93 (t, 1H), 6.81 (s, 1H), 7.04 (s, 1H), 7.12 (s, 1H), 7.66 (s, 1H); m/z 266 (M+H)+

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-22471041e5294b49814fc206e9461657
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902200B2

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