Iodine → Tert-butyl 3-(3-chloro-4-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

HRID 1188188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188188
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([Cl:9])[CH:3]=1.[Mg].II.[C:13]([N:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>O1CCCC1>[Cl:9][C:4]1[CH:3]=[C:2]([C:22]2([OH:25])[CH2:23][CH2:24][N:20]([C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[CH2:21]2)[CH:7]=[CH:6][C:5]=1[F:8]

Komponenten

6

Edukt 4

HCID 807IodineHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 35430654-Bromo-2-chloro-1-fluorobenzeneHCID 5462224Magnesium

Produkt 1

HCID 67402987Tert-butyl 3-(3-chloro-4-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylateAusbeute 41,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Preparation according to Preparation 1. 1-Bromo-3-chloro-4-fluorobenzene (5 g, 23.9 mmol) in dry tetrahydrofuran (100 ml), magnesium turnings (0.57 g, 23.9 mmol) and one crystal of iodine. 1-N-boc-3-pyrrolidone (4.41 g, 23.9 mmol) in dry tetrahydrofuran (50 ml). The crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1) gave the title compound (3.1 g, 41%). MS m/z (rel. intensity, 70 eV) 214 (16), 157 (21), 143 (19), 129 (11), 57 (bp).

Aufarbeitung

  1. customPreparation
  2. customaccording to Preparation 1
  3. customThe crude product was purified by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:9 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7215941065e94b91be0e4fc5d4a53b28
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673962B2

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