126264-10-6

Upstream product

• 38651-65-9 (1R,5S)-(+)-nopinone 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 120633-02-5 N-[(1R,2R,3R,5S)-6,6-Dimethyl-3-(2-oxo-ethyl)-bicyclo[3.1.1]hept-2-yl]-benzenesulfonamide 
• 126264-28-6 (E)-7-((1R,2R,3S,5S)-2-Benzenesulfonylamino-6,6-dimethyl-bicyclo[3.1.1]hept-3-yl)-hept-5-enoic acid; compound with 4-methoxy-benzylamine 
• 120633-07-0 (Z)-7-((1R,2R,3S,5S)-2-Benzenesulfonylamino-6,6-dimethyl-bicyclo[3.1.1]hept-3-yl)-hept-5-enoic acid; compound with 4-methoxy-benzylamine 
• 126264-13-9 (+)-2-((1R,2R,3R,5S)-2-amino-6,6-dimethylbicyclo<3.1.1>hept-3-yl)-ethanol-benzoic acid salt 
• 126264-17-3 (+)-2-((1R,2R,3R,5S)-2-benxenesulfonylamino-6,6-dimethylbicyclo<3.1.1>hept-3-yl)ethanol 

Relevant academic research and scientific papers

Practical diastereoselective synthesis and scale-up study of (+)-2-((1r,2r,3r,5s)-2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)ethanol: A key intermediate of the novel prostaglandin d2 receptor antagonist s-5751

A new synthetic process was developed for (+)-2-((1R,2R,3R,5S)-2-amino-6,6- dimethylbicyclo[3.1.1]hept-3-yl)ethanol, a key intermediate of S-5751. Diastereoselective alkylation of (+)-nopinone with ethyl bromoacetate, formation of O-methyl oxime, and diastereoselective reduction with NaBH4-AlCl3 could be safely carried out. Stereochemistry of the (1R,2R,3R,5S)-6,6- dimethylbicyclo[3.1.1]heptane ring was discussed to achieve high diastereoselectivity on these reactions. For the scale-up, detailed consideration was given to the safety of the NaBH4-AlCl3 reduction.

A general method for the highly diastereoselective, kinetically controlled alkylation of ( )-nopinone

A general method for the monoalkylation of (+)-nopinone was developed for a variety of carbon and heteroatom electrophiles to afford the kinetically controlled product 2 with high diastereoselectivity (98% d.e.) and excellent yield (75-90%).