HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2053533Generated: October 30, 2026
Phenethylamine → tert-butyl (4S,5R)-4,5-diphenyl-2-(2-phenylethylamino)-4,5-dihydroimidazole-1-carboxylate
https://huagongshe.com/reaction/2053533
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenethylamine | HCID 1001 | — |
| Reactant | cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-imidazole-1-carboxylic Acid, Tert-Butyl Ester | HCID 86596320 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | tert-butyl (4S,5R)-4,5-diphenyl-2-(2-phenylethylamino)-4,5-dihydroimidazole-1-carboxylate | HCID 68567764 | 44.2% |
Reaction Steps
A mixture of intermediate 59 (2.0 g, 5.43 mmol), phenethylamine (2.04 mL, 16.3 mmol) and MeOH (0.5 mL) is heated at 100° C. for 2 days. The reaction mixture is cooled to RT, and is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (75:25-60:40) gives 1.06 g of the product 93. 1H NMR (CDCl3) δ 7.40-7.30 (m, 4H), 7.30-7.10 (m, 2H), 7.10-6.90 (m, 8H), 6.80-6.65 (m, 2H), 5.45-5.25 (m, 2H), 3.90-3.60 (m, 2H), 3.05 (t, 2H), 1.13 (s, 9H); MS: m/z 442 (M++1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07326792B2 |
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| Source dataset | uspto-grants-2008_02 |
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| ORD ID | ord-930178231ebc4fd09e6c22fb20478364 |
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| Source note | uspto-grants-2008_02 |
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