Hydrochloric Acid → HCID 53256257, Verbindung

HRID 226341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226341
C(OC(=O)[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:9]1)(C)(C)C.[ClH:22]>CO.CCOC(C)=O>[ClH:22].[ClH:22].[F:20][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:10]2[CH2:11][CH2:12][C@@H:8]([NH2:7])[CH2:9]2)=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 22046331(R)-tert-Butyl (1-(4-fluorobenzyl)pyrrolidin-3-yl)carbamate

Produkt 1

HCID 53256257HCID 53256257, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of (3R)-(+)-3-(tert-butoxycarbonylamino)pyrrolidine (5.0 g) in DMF (50 ml) was added 4-fluorobenzoylchloride (3.38 ml) and N,N-diisopropylethylamine (9.35 ml), the mixture was stirred at 70° C. for 2 hours. The mixed solution was poured into a mixture of water (300 ml) and AcOEt (300 ml). The organic layer was separated, washed with water twice and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with 5% MeOH in dichloromethane to give [1-(4-fluoro-benzyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (6.8 g). To a solution of [1-(4-fluoro-benzyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (6.8 g) in MeOH(34 ml) was treated with 4N HCl in AcOEt (29 ml) and was stirred at 25° C. for 12 hours. The solvent was removed under reduced pressure. Recrystallization (acetonitrile-MeOH) provided (3R)-1-(4-fluorobenzyl)-3-pyrrolidinamine dihydrochloride as white solid (3.77 g).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customRecrystallization (acetonitrile-MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-e21c939a205a4676ba92d9f48a0420ca
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557127B2

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