Methanesulfonyl chloride → Ethyl N-tert-butoxycarbonyl-4-(3-methane-sulfonylaminobenzyl)piperidine-4-carboxylate

A mixture of ethyl N-tert-butoxycarbonyl-4-(3-nitrobenzyl)-piperidine-4-carboxylate (0.85 g, 2.17 mmol; Example 69, Step A) and 5% palladium on charcoal (0.06 g) in ethanol (100 mL) was hydrogenated at room temp. at 50 psi overnight. The resultant mixture was filtered through a plug of Celite, and the filtrate was concentrated under vacuum. The residue was dissolved in pyridine (5 mL), treated with methanesulfonyl chloride (0.24 mL, 3.2 mmol), and heated at 60° C. for 3 h. The product mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluting with 2% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

1. customwas hydrogenated at room temp. at 50 psi overnight
2. filtrationThe resultant mixture was filtered through a plug of Celite
3. concentrationthe filtrate was concentrated under vacuum
4. dissolutionThe residue was dissolved in pyridine (5 mL)
5. concentrationThe product mixture was concentrated under vacuum
6. customCollection and concentration of appropriate fractions

ORD record

ord-37216a9de38a4250be0ef2446c785eca

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248756B1