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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2219682Generated: October 29, 2026

Sodium bis(trimethylsilyl)amide → 4-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester

https://huagongshe.com/reaction/2219682

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium bis(trimethylsilyl)amideHCID 2724254—
ReactantMethyl 4-(3-bromopropyl)benzoateHCID 10801120—
Reactant5-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-oneHCID 12970098—
Product4-(3-{2-[3-(Tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl esterHCID 1297009984.2%

Reaction Steps

Analogous to the procedure described for Compound 1A, Step D, 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-pyrrolidin-2-one (250 mg, 0.602 mmol) was alkylated with NaHMDS (1M in THF, 0.72 mL, 0.72 mmol) and 4-(3-bromo-propyl)-benzoic acid methyl ester (170 mg, 0.663 mmol) to yield 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-trifluoromethyl-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (300 mg). MS 592.1 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07414071B2
Source datasetuspto-grants-2008_08
ORD IDord-84be8e1073c34ace95189eba5bd814c3
Source noteuspto-grants-2008_08