N-(tert-Butoxycarbonyl)-L-leucine methyl ester → tert-butyl N-(4-methyl-1-oxopentan-2-yl)carbamate

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Reaktionsgleichung

C[O:2][C:3](=O)[C@H:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[H-].C([Al+]CC(C)C)C(C)C>>[C:9]([O:8][C:6]([NH:5][CH:4]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH:3]=[O:2])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Komponenten

Edukt 2

HCID 10879384N-(tert-Butoxycarbonyl)-L-leucine methyl ester

HCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 546109tert-butyl N-(4-methyl-1-oxopentan-2-yl)carbamate

Versuchsvorschrift

t-Butoxycarbonyl-L-leucine methyl ester was reduced with diisobutylaluminium hydride in an analogous manner to that described in Example 1 to give 2-t-butoxycarbonylamino-4-methyl-valeraldehyde, which was used directly in the next step without further purification.

Quellen und Nachweise

ORD-Eintrag: ord-b9598c68c91c485ebe1810fd72e62cc5
Quelldatensatz: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05250517

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