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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 422925Generated: October 30, 2026

Diethyl Ether → (2R)-2-t-Butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butanal

https://huagongshe.com/reaction/422925

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantCornforth reagentHCID 2724130—
Reactant(2R)-2-t-Butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-olHCID 66672878—
SolventDichloromethaneHCID 6344—
Product(2R)-2-t-Butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-1-butanalHCID 8659670563%

Reaction Steps

To a solution of (2R)-2-t-butoxycarbonylamino-2-methyl-4-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]butan-1-ol (0.3520 g, 0.80 mmol) obtained in Example (43a) in dichloromethane (8 ml) were added successively molecular sieves 4A (0.2234 g) and pyridinium dichromate (0.4594 g, 1.22 mmol), and the resulting mixture was stirred at room temperature for 20 hours. After stirring, ether was added to the reaction mixture, and the resulting mixture was filtered. The filtrate was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (3:2) as the eluent to afford the title compound (0.2195 g, yield: 63%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08101650B2
Source datasetuspto-grants-2012_01
ORD IDord-db7aba8fcfea4a45af3be3ec999bb203
Source noteuspto-grants-2012_01