I'm not sure of this nomenclature and ChemDraw is of specific help. It doesn't give the option of giving a correct nested name. It uses t-butyl instead.
If you had 2-t-butylcyclopentanol, it could also be named as 2-(1,1-dimethylethyl)cyclopentanol. I used to refer to the (1,1-dimethylethyl) as a nested name (I don't know if there is an official way to name this type of name). ChemDraw gives a name 4-(tert-butyl)nonane for 4-(1,1-dimethylethyl)nonane. Note how the name is nested upon ethyl. I don't know if parentheses are needed or not, but with ethyl, a locus is not needed as changing the locus changes the compound. It can only be 1,1-dimethylethyl as 1,1-dimethyl-2-ethyl would be 2-methylpropyl.