HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1295727Generated: October 30, 2026
Ethylene Glycol → tert-butyl (3R)-4-[3-(2-hydroxyethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate
https://huagongshe.com/reaction/1295727
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | (R)-tert-butyl 4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate | HCID 86591091 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | tert-butyl (3R)-4-[3-(2-hydroxyethoxy)pyrazin-2-yl]-3-methylpiperazine-1-carboxylate | HCID 69366745 | 87% |
Reaction Steps
A mixture of tert-butyl (3R)-4-(3-chloropyrazin-2-yl)-3-methylpiperazine-1-carboxylate* (35 g, 0.11 mol), ethylene glycol (100 g, 1.61 mol) and t-BuOK (25 g, 0.22 mol) in DMSO (150 g) was stirred at 50° C. for 3 h. After this time, the reaction mixture was partitioned between EtOAc (500 g) and water (500 g) and sodium chloride (20 g) was added. The organic layer was concentrated in vacuo to furnish 32.5 g (87%) of the title product. HPLC purity: 75%. HRMS m/z calcd for C16H26N4O4 (M)+ 338.1954, found 338.1959. *Described in WO 00/76984, Example 172, Step 2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07244722B2 |
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| Source dataset | uspto-grants-2007_07 |
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| ORD ID | ord-0e0738a5d6b84072a849fcf60a9332a9 |
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| Source note | uspto-grants-2007_07 |
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