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3 Polish Journal of Chemistry

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An Expedient Transformation of Alcohols into N-Boc-Amines

Śliwińska A., Zwierzak A.

Polish Journal of Chemistry

2004

Vol.78 /nr 11-12

2127-2130

t-Butyl methyl iminodicarbonate (3) can be easily alkylated with primary or secondary alcohols under Mitsunobu conditions (DIAD, TPP) to give the corresponding N-alkyl iminodicarbonates. Partial deprotection of the latter with methanolic potassium hydroxide affords N-Boc-amines (5) in good yields.

Simple Approach to 1-Alkyl-2-isopropylhydrazines

Zawadzki S., Zwierzak A.

Polish Journal of Chemistry

2003

Vol. 77 / nr 3

315-319

Ditosylates of 1-alkyl-2-isopropylhydrazines were prepared by N-alkylation of t-butyl isopropylidenecarbazate (2) followed by reduction of N-alkyl-t-butyl isopropylidenecarbazate (3) with lithium aluminum hydride in boiling tetrahydrofuran. The removal of N-Boc protecting group was quantitatively achieved by refluxing N-alkyl-t-butyl isopropylcarbazate (4) with p-toluenesulfonic acid monohydrate in dichloromethane.

New Approach to Tertiary Carbinamines

Gajda T., Koziara A., Napieraj A., Sikora D., Zwierzak A.

Polish Journal of Chemistry

2000

Vol. 74, nr 10

1385-1385

Tertiary carbinamines (t-alkyl amines) can be conveniently obtained by dephosphorylation of diethyl N-t-alkylphosphoramidates 1 with 20% hydrochloric acid-tetrahydrofuran (1:1 v/v)