Triethylamine → 1'-(1,1-Dimethylethyloxycarbonyl)-3-[[[methoxycarbonyl]-methyl]sulfonyl]amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine)

Participants

Reaction Steps

A sample of 1'-(1,1-dimethylethyloxycarbonyl)-3-amino-2,3-dihydrospiro(1H-indene-1,4'-piperidine), prepared by hydrogenation of 500 mg of oxime (1.58 mmole) as in Example 135, in 2 mL methylene chloride containing 475 mg of DMAP (2.46×1.58 mmole), and 550λ of triethylamine (2.51×1.58 mmole), was stirred under nitrogen in an ice bath while adding a solution of 400λ of 8.4M methyl chlorosulfonylacetate (2.13×1.58 mmole) in 2 mL methylene chloride dropwise over 2-3 minutes. The suspension was stored over night in the refrigerator. It was then washed twice with water, then with 5% citric acid. Atypically, solid material was still present in suspension; this was s removed by filtration, the filtrate dried with magnesium sulfate and concentrated under reduced pressure. Again, solid formed and was removed by filtration. Finally, preparative TLC on four 8"×8"×1,000μ GF silica gel plates using 2:1 ethyl acetate:hexane afforded 389 mg of the title compound

Provenance & Evidence