Sodium hydride → tert-butyl (3RS,4RS)-3-naphthalen-2-ylmethoxy-4-(4-trityloxymethyl-phenyl)-piperidine-1-carboxylate

290 mg (6.05 mmol) of sodium hydride (50% dispersion in refined oil) were added to a solution of 2.08 g (3.78 mmol) of tert-butyl (3RS,4RS)-3-hydroxy-4-(4-trityloxymethyl-phenyl)-piperidine-1-carboxylate and 1.0 g (4.54 mmol) of 2-bromomethylnaphthalene in 30 ml of dimethylformamide and the reaction mixture was stirred at room temperature for 2 hours. For the working-up, the reaction mixture was evaporated in an oil pump vacuum, the residue was partitioned between 100 ml of saturated ammonium chloride solution and 100 ml of ethyl acetate and thereafter the separated aqueous phase was extracted twice with 50 ml of ethyl acetate each time. The combined ethyl acetate extracts were dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a 4:1 mixture of methylene chloride and hexane as the eluent. There were obtained 2.27 g (87% of theory) of tert-butyl (3RS,4RS)-3-naphthalen-2-ylmethoxy-4-(4-trityloxymethyl-phenyl)-piperidine-1-carboxylate as a colourless solid; MS: 707 (M+NH4)+.

1. customthe reaction mixture was evaporated in an oil pump vacuum
2. customthe residue was partitioned between 100 ml of saturated ammonium chloride solution and 100 ml of ethyl acetate
3. extractionthe separated aqueous phase was extracted twice with 50 ml of ethyl acetate each time
4. dry with materialThe combined ethyl acetate extracts were dried over sodium sulphate
5. customevaporated under reduced pressure
6. customFor purification
7. customthe crude product was chromatographed on silica gel using
8. additiona 4:1 mixture of methylene chloride and hexane as the eluent

ORD record

ord-58acd74d91cc44ce9dd3225f3a8034d7

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06150526