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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 928006Generated: October 30, 2026

Methanol → HCID 86713334, compound

https://huagongshe.com/reaction/928006

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactanttert-Butyl 3-{[(benzyloxy)(hydroxy)methylidene]amino}pyrrolidine-1-carboxylateHCID 12184171—
SolventTetrahydrofuranHCID 8028—
ProductHCID 86713334HCID 8671333491.9%

Reaction Steps

Sodium hydride (60% oil dispersion, 0.32 g) was added to a stirred solution of tert-butyl (S)-3-benzyloxycarbonylaminopyrrolidine-1-carboxylate (prepared according to Cheng et al, WO2007 142585, 1.73 g) in THF (20 mL) and the mixture was stirred for 15 minutes. Iodomethane (1.85 g) was added and the mixture was stirred at room temperature for 1 hour. Methanol was carefully added to destroy the excess sodium hydride then ethyl acetate and water were added and the organic layer was washed with brine, dried (Na2SO4), filtered. The filtrate was concentrated in vacuo to give tert-butyl (S)-3-(N-benzyloxycarbonyl-N-methylamino)pyrrolidine-1-carboxylate (1.66 g) as a pale coloured oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09290472B2
Source datasetuspto-grants-2016_03
ORD IDord-4ddb955915904e899aa09e807c6de1f7
Source noteuspto-grants-2016_03