Science of Synthesis

Lawrence, S. A., Science of Synthesis, (2009) 40, 511.

The N-(triphenylmethyl) (N-trityl) residue and the related N-(9-phenyl-9H-fluoren-9-yl) group are easily removed from amines by treatment with dilute acid making them convenient protective groups for the amine function.[‌47‌] In a synthetic application, alkylamine hydrochlorides ‌26‌ can be easily prepared in high yields from the reaction of alkyl halides with tritylamine to give alkyl(trityl)amines ‌25‌, from which the trityl group is removed using trifluoroacetic acid in dichloromethane (‌Scheme 16‌).[‌48‌]

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M8M	Meeee (MeMM8/M8M)	Meeeeeeeee	Meeee (%) ee ‌88‌	Mee
MeM	8:8	MeMM, 8 e, ee	88	[‌88‌]
Me	8:88	MeMM, 88 e, ee	88	[‌88‌]
MM≡MMM8Me	8:8	MeMM, 8 e, ee	88	[‌88‌]
Me(MM8)8MMe	8:8	Me8M, eeeeeee, 88 e, eeeeee	88	[‌88‌]
	8:8	MeMM, 8 e, 88°Me	88	[‌88‌]
MeMe	8:8	MeMM, 8 e, ee	88	[‌88‌]
Me(MM8)MMe	8:8	Me8M, eeeeeee, 88 e, eeeeee,	88	[‌88‌]

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References

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• 8.Meeeee-Meee, (8888) 88/8, 888.