Reaktion #363839

Reaktionsgleichung

2-hydroxyethylamine

isobutyraldehyde

2-Methyl-4-nitroaniline

3-Aminotetrahydro-2H-pyran-3-carboxylic acid

formanilide

Methyl 3-aminotetrahydro-2H-pyran-3-carboxylate

3-amino-3-(hydroxymethyl)tetrahydro-2H-pyran

→

2-isopropyl-1-aza-3,7-dioxaspiro[4.5]decane

Reaktionsbedingungen

Vorschrift

2-Methyl-4-nitroaniline was converted to the 2-methyl-4-nitroformanilide according to Method A3a, Step 1. The formanilide was converted to 2-methyl-4-nitrophenyl isocyanide dichloride according to Method A3a, Step 2. 3-Aminotetrahydro-2H-pyran-3-carboxylic acid was converted to the methyl ester according to Method B1b, Step 1. Methyl 3-aminotetrahydro-2H-pyran-3-carboxylate was reduced to 3-amino-3-(hydroxymethyl)tetrahydro-2H-pyran according to Method B1b, Step 2. The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford 2-isopropyl-1-aza-3,7-dioxaspiro[4.5]decane. The oxazolidine was reduced to 3-isobutylamino-3-(hydroxymethyl)tetrahydro-2H-pyran. The substituted 2-hydroxyethylamine was converted to 3-isobutylamino-3-(acetylthiomethyl)tetrahydro-2H-pyran according to Method C6c, Step 1. The thioacetate was saponified according to Method C6c, Step 2 to give 3-isobutylamino-3-(thiomethyl)tetrahydro-2H-pyran. The 2-thioethylamine was reacted with 2-methyl-4-nitrophenyl isocyanide dichloride to afford 2-(2-methyl-4-nitrophenylimino-1-isobutyl-1-aza-7-oxa-3-thiaspiro[4.5]decane.

Quelle