Sodium borohydride → alpha-Methylisoquinoline-3-methanol

HRID 1637750

Reaktionsgleichung

[C:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[N:5]=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

3-Acetyl-isoquinoline (1.53 g, 8.9 mmole) is dissolved in 42 ml methanol in a 100 ml one neck round bottom flask at 0° C. The solution is treated portionwise with sodium borohydride (388 mg, 10.3 mmole) and the reaction mixture is stirred 30 min at 0° C. The volatiles are removed in vacuo and the residue is partitioned between 1×100 ml 1N sodium hydroxide and 3×25 ml dichloromethane. The combined organics are dried over potassium carbonate and are concentrated in vacuo to a pale yellow solid. The crude material is chromatographed over 60 g silica gel (230-400 mesh), eluting with 40% acetone/hexane, while collecting 9 ml fractions. Fractions 26-45 are combined and concentrated to afford 1.23 g (80%) of 3-(1-hydroxyethyl)-isoquinoline.

Aufarbeitung

customThe volatiles are removed in vacuo
customthe residue is partitioned between 1×100 ml 1N sodium hydroxide and 3×25 ml dichloromethane
dry with materialThe combined organics are dried over potassium carbonate
concentrationare concentrated in vacuo to a pale yellow solid
customThe crude material is chromatographed over 60 g silica gel (230-400 mesh)
washeluting with 40% acetone/hexane
customwhile collecting 9 ml fractions
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-55e7e01a2262485a807e4d02438b7ea1
Quelldatensatz: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06043248

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