(+/-)-(2R,3R)-1-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-[(1R)-1-(3-chloro-4-cyano-2-methylphenylamino)ethyl]piperidine → 4-[(1S,7R,7aR)-7-Hydroxy-1-methyl-3-oxohexahydropyrrolo[1,2-c]imidazol-2-yl]-2-chloro-3-methylbenzonitrile

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Reaction Steps

Compounds 81A-a and 81A-b were synthesized from 1-tert-butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-formyl-piperidine (18F) following a procedure similar to that used for 80F to give a mixture of 81A-a and 81A-b as the crude product. Purification and separation by flash chromatography (12 g ISCO silica gel column, 0-20% EtOAc/hexane gradient) provided 81A-a as colorless film (28 mg) and 81A-b (14 mg) as a colorless film. For 81A-a: HPLC (Phenomenex Luna 5 u C18 4.6×50 mm, linear gradient over 4 min) retention time 4.85 min (100%); MS (ES) m/z 508.0 [M+H]+; HRMS calcd for C26H43ClN3O3Si 508.2762, Found 508.2761. For 81A-b: HPLC (Phenomenex Luna 5 u C18 4.6×50 mm, linear gradient over 4 min) retention time 4.95 min (100%); MS (ES) m/z 508.0 [M+H]+; HRMS calcd for C26H43ClN3O3Si 508.2762, Found 508.2748.

Provenance & Evidence