Tert-butyl 3-oxopyrrolidine-1-carboxylate → Tert-butyl 3-(3-chloro-2-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

HRID 575980

Reaktionsgleichung

Reaktionsgleichung von HRID 575980
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[F:9].C([Li])CCCCC.[C:17]([N:24]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25]1)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>C(OCC)C>[Cl:8][C:4]1[C:3]([F:9])=[C:2]([C:26]2([OH:29])[CH2:27][CH2:28][N:24]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:25]2)[CH:7]=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 36857621-Bromo-3-chloro-2-fluorobenzeneHCID 178506865HCID 178506865, Verbindung

Produkt 1

HCID 67404349Tert-butyl 3-(3-chloro-2-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylateAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Preparation according to Preparation 10: 1-Bromo-3-chloro-2-fluorobenzene (8 g, 38.3 mmol), dry diethyl ether (100 mL), n-hexyllithium (2.3 M in hexane, 16.64 ml, 38.3 mmol) and a solution of 1-N-boc-3-pyrrolidone (7.08 g, 38.3 mmol) in dry diethyl ether (50 mL). The crude product was purified by flash column chromatography (ethylacetate/isooctane, 1:9 to 1:1) to give the title compound (8.05 g, 66%). MS m/z (rel. intensity, 70 eV) 259 (20), 214 (42), 157 (26), 143 (23), 57 (bp).

Aufarbeitung

  1. customPreparation
  2. customaccording to Preparation 10
  3. customThe crude product was purified by flash column chromatography (ethylacetate/isooctane, 1:9 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-9ad73f186c06427b9948d8953086d6cf
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09035073B2

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