Patent ID: 7326787

Claim:
A process for preparing (R)-quinuclidin-3-yl 6-((3S,4R)-4-(4-amino-5-chloro-2-methoxybenzamido)-3-methoxypiperidin-1-yl)hexanoate or a salt thereof, comprising: 1) converting a compound that is ethyl 4-amino-3-methoxypiperidine-1-carboxylate to a salt; 2) converting the ethyl 4-amino-3-methoxypiperidine-1-carboxylate salt to ethyl 4-(dibenzylamino)-3-methoxypiperidine-1-carboxylate 3) treating the ethyl 4-(dibenzylamino)-3-methoxypiperidine-1-carboxylate with an alkali metal hydroxide to yield 3-methoxy-N,N-dibenzylpiperidin-4-amine 4) preparing a chiral salt of the cis isomer of 3-methoxy-N,N-dibenzylpiperidin-4-amine by contacting 1 equivalent of 3-methoxy-N,N-dibenzylpiperidin-4-amine with about 0.5 equivalents of a chiral resolving agent and isolating the chiral salt of the cis isomer of 3-methoxy-N,N-dibenzylpiperidin-4-amine thereby produced; 5) optionally recrystallizing the product of step 4; 6) basifying the product of 4 or 5 to yield the free base form of the product of step 4 or 5 7) contacting the product of step 5 with ethyl 6-bromohexanoate to yield ethyl 6-((3S,4R)-4-(dibenzylamino)-3-methoxypiperidin-1-yl)hexanoate 8) esterifying the ethyl 6-((3S ,4R)-4-(dibenzylamino)-3-methoxypiperidin-1-yl)hexanoate with (R)-quinuclidin-3-ol and a Lewis acid to yield (R)-quinuclidin-3-yl 6-((3S,4R)-4-(dibenzylamino)-3-methoxypiperidin-1-yl)hexanoate 9) deprotecting the 4-amino group of the product of step 8 to yield (R)-quinuclidin-3-yl 6-[(3S ,4R)-4-amino-3-methoxypiperidin-1-yl]hexanoate; 10) acylating the product of 9 with 4-amino-5-chloro-2-methoxybenzoic acid to yield (R)-quinuclidin-3-yl 6-((3S,4R)-4-(4-amino-5-chloro-2-methoxybenzamido)-3-methoxypiperidin-1-yl)hexanoate; and 11) optionally converting the product of step 10 to a salt.