Sodium Hydroxide → methyl 3-(S)-((2-methoxy-5-(1-tetrazolyl)phenyl)methylamino)-2-(R)-(4-fluorophenyl)cyclopentane-1-(R)-carboxylate

Participants

Reaction Steps

To a solution of 100 mg of amine from Example 62 in 2 mL of methanol was added 0.040 mL of acetic acid, 1 g of 3A sieves and 90 mg 2-methoxy-5-(1-tetrazolyl)benzaldehyde (prepared according to the procedures given in PCT International Application WO 95/08549, published 30 Mar. 1995; p. 33). The reaction was stirred at room temperature for 30 min and then 0.080 g of sodium cyanoborohydride was added. The reaction was stirred further for 20 h and was then poured into water, made basic with 2N NaOH and extracted twice with ether. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography eluting with 0 to 3% methanol in methylene chloride to obtain 100 mg of title compound.

Provenance & Evidence