Cyclopropanesulfonyl chloride → Ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentanecarboxylate

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Reaction Steps

The precursor to Preparation #Z.1, (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate, was prepared (as shown in Scheme B) by initially reacting ethyl 4-amino-2-ethylcyclopentanecarboxylate (Preparation #Y.1) with the commercially available cyclopropanesulfonyl chloride, following the conditions given in General Procedure K, to give ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate as a mixture of stereoisomers. This mixture of stereoisomers is separated as described in General Procedure AA, using the conditions from Method 1 in Table 2, to give the precursor to Preparation #Z.1, (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate as a single enantiomer with a retention time of 9.5 minutes and a negative optical rotation. The reaction sequence to synthesize the precursor to Preparation #Z.1, (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate, (detailed above) is consequently translated in the preparations and examples section to: (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane-carboxylate (prepared using K from Preparation #Y.1 and cyclopropanesulfonyl chloride, AA [Table 2, Method 1, Rt=9.5 min, or =negative]). Hence the Preparation #Z.1 would be written as: Preparation #Z.1 was prepared from (1S,2R,4S)-ethyl 4-(cyclopropanesulfonamido)-2-ethylcyclopentane carboxylate (prepared using K from Preparation #Y.1 and cyclopropanesulfonyl chloride, AA [Table 2, Method 1, Rt=9.5 min, or =negative]) using General Procedure Z.

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