Water → Methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamate

HRID 2068997

Reaktionsgleichung

Reaktionsgleichung von HRID 2068997
[BH4-].[Na+].[Br-].[CH2:4]([N+:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([NH:18][C:19]([O:21][CH3:22])=[O:20])[CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CO>[CH2:4]([N:11]1[CH2:16][CH2:15][C:14]([CH3:17])=[C:13]([NH:18][C:19](=[O:20])[O:21][CH3:22])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 667702031-Benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide

Produkt 1

HCID 58526548Methyl 1-benzyl-4-methyl-1,2,5,6-tetrahydropyridin-3-ylcarbamateAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium borohydride (4.4 g, 116 mmol, 1.20 equiv.) was added in several batches to a solution of 1-benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide (35 g, 104 mmol, 1.00 equiv.) in methanol (300 mL). The resulting solution was stirred at ambient temperature for about 16 hours, and then water (200 mL) was added. After concentrating the mixture in vacuo, standard extractive workup with ether (3×200 mL) gave a crude residue that was then purified by silica gel column chromatography (dichloromethane/methanol (20:1)) to afford the title product as a yellow solid (18 g; yield=66%). LC-MS: m/z=261 (M+H)+.

Aufarbeitung

  1. concentrationAfter concentrating the mixture in vacuo, standard extractive workup with ether (3×200 mL)
  2. customgave a crude residue that
  3. customwas then purified by silica gel column chromatography (dichloromethane/methanol (20:1))

Quellen und Nachweise

ORD-Eintrag
ord-4b3621c424864c319cffa80e57599381
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299084B2

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