Sodium borohydride → 2-(7-Fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pyrrolidine

HRID 2167736

Reaktionsgleichung

Reaktionsgleichung von HRID 2167736
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:14]2[CH2:15][CH2:16][CH2:17][N:18]=2)[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1>CO.O>[F:3][C:4]1[CH:5]=[C:6]([CH:14]2[CH2:15][CH2:16][CH2:17][NH:18]2)[C:7]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:13]=1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 896184245-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-3,4-dihydro-2H-pyrrole

Produkt 1

HCID 896182762-(7-Fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

NaBH4 (0.25 g, 6.69 mmol) was added to a solution of 5-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-3,4-dihydro-2H-pyrrole (Int-55) (0.8 g, 3.34 mmol) in a mixture of MeOH and H2O (3:1, 20 mL) and was stirred at 25° C. for 2 h. Reaction mixture was quenched with 1N aqueous HCl solution (50 mL) and basified with 2N aqueous NaOH solution to pH 8 and extracted with DCM (3×20 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 2-(7-fluoro-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)pyrrolidine (Int-56). MS (ESI) m/z 224.5 (M+H).

Aufarbeitung

  1. customReaction mixture
  2. customwas quenched with 1N aqueous HCl solution (50 mL)
  3. extractionextracted with DCM (3×20 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fef83ab4e87c4bb0ae0185eac25a1690
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045478B2

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