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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1015570Generated: October 31, 2026

Chlorotrimethylsilane → (2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile

https://huagongshe.com/reaction/1015570

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChlorotrimethylsilaneHCID 6397—
Reactant(2S)-1-{N-[2-(2-oxopyrrolidin-1-yl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrileHCID 24853439—
SolventMethanolHCID 887—
Product(2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrileHCID 24853441217.5%

Reaction Steps

To a stirred solution of the compound obtained from example 26 (35 mg, 0.1 mmol) in methanol (2 mL) cooled to 0° C. was added TMS-Cl (25 μL, 0.2 mmol). After 30 minutes, the volatiles were removed under reduced pressure and the residue was triturated several times with diethyl ether to obtain the hydrochloride salt of (2S)-1-[N-(2-phenylhexahydro-2,5-methanopentalen-3a(1H)-yl)glycyl]pyrrolidine-2-carbonitrile as an off-white solid (38 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07985759B2
Source datasetuspto-grants-2011_07
ORD IDord-370219fe08c84fd2a08708055629c403
Source noteuspto-grants-2011_07