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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1869667Generated: October 31, 2026

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

https://huagongshe.com/reaction/1869667

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 4 A (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 numberUS07638551B2
Source datasetuspto-grants-2009_12
ORD IDord-abe5c5f7109f46fa82495c574c578897
Source noteuspto-grants-2009_12