HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 1'-({6-Chloro-1-[(3S)-piperidin-3-ylmethyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (S)-[[(Methylsulfonyl)oxy]methyl]piperidine-1-carboxylic Acid tert-Butyl Ester | HCID 10469651 | — |
| Reactant | (6-chloro-1H-indol-3-yl)-spiro[1H-2-benzofuran-3,4'-piperidine]-1'-ylmethanone | HCID 15951937 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1'-({6-Chloro-1-[(3S)-piperidin-3-ylmethyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine] | HCID 59657538 | 39% |
Reaction Steps
A solution of the 1′-[(6-chloro-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] (prepared according to example 69) in dry DMF was treated with NaH (1.1 eq) and stirred for 10 min at room temperature, then treated with (S)-3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (1.1 eq) (JP 2001278872) and stirred at room temperature for 16 h then 70° for 4 h. Concentration and treatment with excess HCl in dioxane gave after purification by preparative HPLC the desired product in 39% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07629353B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-87dc7c165f5f4ba5adbdf79217708c73 |
| Source note | uspto-grants-2009_12 |