HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl bromide → 1-(Prop-2-yn-1-yl)pyrrolidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl bromide | HCID 7842 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | 1-(Prop-2-yn-1-yl)pyrrolidine | HCID 299616 | — |
| Reactant | 8-tert-Butoxycarbonylamino-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indole-2-carboxylic acid methyl ester | HCID 136181612 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 1-(Prop-2-yn-1-yl)pyrrolidine | HCID 299616 | — |
| Product | (1r,2r)-2-Phenyl-cyclopropanecarboxylic acid [6-oxo-2-(3-pyrrolidin-1-yl-prop-1-ynyl)-5,6-dihydro-1h-[1,2]diazepino[4,5,6-cd]indol-8-yl]-amide | HCID 136141754 | — |
Reaction Steps
Preparation of example 247 from Intermediate 147(d) of Example 147 (300 mg, 0.794 mmol) was carried out in three steps in a manner similar to that described for the preparation of Example 233 except that 1-prop-2-ynyl-pyrrolidine was used instead of dimethyl-prop-2-ynyl-amine in step 1. 1-Prop-2-ynyl-pyrrolidine was prepared by stirring 3-bromo-propyne, pyrrolidine and triethylamine at room temperature in tetrahydrofuran for 2 hours. The title compound (80 mg, 0.177 mmol) was obtained as a yellow powder in 36% overall yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07132533B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-49781bcfde9947c69548695215e46acf |
| Source note | uspto-grants-2006_11 |