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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 23452Generated: October 26, 2026

Diisopropylamine → 3-Hydroxy-4-methyl-3-(2-thiophen-3-yl-ethyl)-pentanoic Acid Tert-Butyl Ester

https://huagongshe.com/reaction/23452

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylamineHCID 7912—
Reactanttert-Butyl acetateHCID 10908—
Reactant4-Methyl-1-thiophen-3-yl-pentan-3-oneHCID 12477279—
ReactantButyllithiumHCID 178418339—
SolventTetrahydrofuranHCID 8028—
Product3-Hydroxy-4-methyl-3-(2-thiophen-3-yl-ethyl)-pentanoic Acid Tert-Butyl EsterHCID 57227617—

Reaction Steps

The title compound was prepared as described in General Method 9 using t-butyl acetate (42.6 mmol), diisopropyl amine (42.6 mmol), nBuLi (42.6 mmol), 4-methyl-1-thiophen-3-yl-pentan-3-one (Example C-5; 21.3 mmol), and THF (100 mL). The title compound was purified by flash chromatography over silica gel eluting with hexane:EtOAc 97:3. 1NMR (CDCl3): δ 0.95 (dd, 6H), 1.47 (s, 9H), 1.7-2.0 (m, 3H), 2.36-2.54 (AB q, 2H), 2.6-2.8 (m, 2H), 6.93-6.95 (m, 2H), 7.23-7.25 (m, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06852711B2
Source datasetuspto-grants-2005_02
ORD IDord-5aa23f0d6d004be186f9a6de446d51d1
Source noteuspto-grants-2005_02