Accelerator DM → tert-butyl (3RS,4RS)-4-[4-[3-(benzothiazol-2-ylsulfonyl)-propoxy]-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Participants

Reaction Steps

In an analogous manner to that described in Example 1 (g), by alkylating a mixture of tert-butyl (3RS,4RS)- and (3SR,4SR)-3-hydroxy-4-[4-[3-[(RS)-tetrahydro-pyran-2-yloxy]-propoxy]-phenyl]-piperidine-1-carboxylate [Example 57 (a)] with 1-methoxy-2-bromomethyl-naphthalene [Example 7 (f)] there was obtained a mixture of tert-butyl (3RS,4RS)- and (3SR,4SR)-3-(1-methoxy-naphthalen-2-ylmethoxy)-4-[4-[3-[(RS)-tetrahydro-pyran-2-yloxy]-propoxy]-phenyl]-piperidine-1-carboxylate. Cleavage of the THP group by means of pyridinium (toluene-4-sulphonate) in ethanol analogously to Example 53 (c) gave tert-butyl (3RS,4RS)-4-[4-(3-hydroxy-propoxy)-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate, reaction of which with bis-(benzothiazol-2-yl) disulphide analogously to Example 33 (a) gave tert-butyl (3RS,4RS)-4-[4-[3-(benzothiazol-2-ylsulphonyl)-propoxy]-phenyl]-3-(1-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless liquid; MS: 671 (M+H)+.

Provenance & Evidence