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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 489159Generated: October 29, 2026

Methanol → {(Z)-4-[(R)-2-(3-Hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-but-2-enyloxy}-acetic acid methyl ester

https://huagongshe.com/reaction/489159

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantSodium borohydrideHCID 4311764—
Reactant{(Z)-4-[(R)-2-Oxo-6-(3-oxo-4-phenyl-butyl)-piperidin-1-yl]-but-2-enyloxy}-acetic acid methyl esterHCID 11749537—
SolventDichloromethaneHCID 6344—
Product{(Z)-4-[(R)-2-(3-Hydroxy-4-phenyl-butyl)-6-oxo-piperidin-1-yl]-but-2-enyloxy}-acetic acid methyl esterHCID 1137270487%

Reaction Steps

Sodium borohydride (2 mg, 0.053 mmol), followed by MeOH (0.15 mL), was added to a solution of {(Z)-4[(R)-2-oxo-6-(3-oxo-4-phenyl-butyl)-piperidin-1-yl]-but-2-enyloxy}-acetic acid methyl ester (11.5 mg, 0.030 mmol) in CH2Cl2 (0.5 mL) at 0° C. The mixture was allowed to warm to rt. After 30 min at rt, the reaction was quenched with aqueous HCl (0.5 M) and extracted with EtOAc (3×7 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford 10.1 mg (87%) of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06977260B2
Source datasetuspto-grants-2005_12
ORD IDord-f4b286e3fdff497cbfe0a07f248e4375
Source noteuspto-grants-2005_12