Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (3S)-1-[(tert-butoxy)carbonyl]pyrrolidine-3-carboxylic acid | HCID 1512492 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-[4-(Benzyloxy)-3-methoxyphenyl]methanamine--hydrogen chloride (1/1) | HCID 16247759 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 27866014 | HCID 27866014 | 69.4% |
Reaction Steps
1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.12 g) was added to a mixture of 4-benzyloxy-3-methoxybenzylamine hydrochloride (1.26 g), (S)-1-(t-butoxycarbonyl)pyrrolidine-3-carboxylic acid (0.97 g), triethylamine (0.82 ml) and methylene chloride (20 ml). After stirring the reaction mixture at room temperature for 20 hours, the mixture was washed with saturated ammonium chloride aqueous solution and then saturated brine, the organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: hexane/ethyl acetate=100/0 to 0/100 gradient) to obtain 1.42 g of t-butyl (S)-3-(4-benzyloxy-3-methoxybenzylcarbamoyl)-piperidine-1-carboxylate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08367835B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-d3a4482c5e4647ba810198af6a42f1b1 |
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| Source note | uspto-grants-2013_02 |
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