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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 69486Generated: October 25, 2026

Ethyl Acetate → 2-Methyl-1-[(R)-1-(2-methyl-4-nitro-phenyl)-pyrrolidin-3-ylamino]-propan-2-ol

https://huagongshe.com/reaction/69486

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantIsobutylene oxideHCID 11208—
ReactantLithium BromideHCID 82050—
Reactant(R)-1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-3-ylamineHCID 68687704—
SolventWaterHCID 962—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product2-Methyl-1-[(R)-1-(2-methyl-4-nitro-phenyl)-pyrrolidin-3-ylamino]-propan-2-olHCID 68991896—

Reaction Conditions

Temperature80 °C

Reaction Steps

LiBr (153.6 mg) and isobutylene oxide (85.1 mg) were added to a solution of (R)-1-(2-fluoro-4-nitro-phenyl)-pyrrolidin-3-ylamine (100 mg) in NMP (2 mL) and the reaction mixture was heated for 2 d at 80° C. Then ethyl acetate and water were added to the mixture. The aqueous phase was extracted several times with ethyl acetate. The organic phases were combined, dried over sodium sulfate and the solvent was removed in vacuum. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 297.15 (C14H20FN3O3); MS (ESI): 298 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822495B2
Source datasetuspto-grants-2014_09
ORD IDord-c9b57c8025e042e8b0831d2a6c1beb41
Source noteuspto-grants-2014_09