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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1068165Generated: November 1, 2026

Sodium triacetoxyborohydride → alpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester

https://huagongshe.com/reaction/1068165

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium triacetoxyborohydrideHCID 5049666—
Reactant1-Piperidin-4-yl-5-fluoro-1-H-benzoimidazoleHCID 21193111—
Reactantalpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl esterHCID 53654320—
SolventDimethylformamideHCID 6228—
SolventTetrahydrofuranHCID 8028—
Productalpha-(R)-(3-(S)-((4-(5-Fluoro-benzoimidazol-1-yl)-piperidin-1-ylmethyl))-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl esterHCID 8675702673.3%

Reaction Steps

The title compound was prepared from 40 mg of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (prepared above as Aldehyde 5), 40 mg 1-piperidin-4-yl-5-fluoro-1-H-benzoimidazole (from Step C ) and 60 mg of sodium triacetoxyborohydride in 4 mL of THF and 1 mL of DMF, using a procedure analogous to that described in Example 95, Step D to provide 43 mg of the title compound as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06248755B1
Source datasetuspto-grants-2001_06
ORD IDord-870ecb71469e44fa9ffa6f8faec9bdf1
Source noteuspto-grants-2001_06