HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Benzoic acid, 4-amino-, 1,1-dimethylethyl ester | HCID 233272 | — |
| Catalyst | Cupric Chloride | HCID 24014 | — |
| Product | Methyl 3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate | HCID 15480266 | 92% |
Reaction Steps
1.5 grams (3.77 mMoles) of Fmoc-citruline were dissolved in 3 mL of DMF in a round bottom flask to which was added 0.87 grams (4.5 mMoles) of EDC, 0.61 grams (4.5 mMoles) of HOBt. 6 mL of DCM were then added followed by the addition 0.88 grams (4.5 mMoles) of t-butyl-4-aminobenzoate and a catalytic amount of copper chloride. The reaction mixture was allowed to stir overnight The solvents were evaporated and the crude product purified over silica gel with 5 to 10% MeOH in DCM to give 2 grams of 4 in 92% yield. M+1=574
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461117B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-1e6d4896c0cb4012b6cb5a86bfccf778 |
| Source note | uspto-grants-2013_06 |