HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Iodide → 5-(4-Fluorobenzyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Chloroacetyl chloride | HCID 6577 | — |
| Reactant | Iodide Ion | HCID 30165 | — |
| Reactant | 2-Methylpropan-2-olate | HCID 4574913 | — |
| Reactant | 4-[1-Amino-2-(4-fluorophenyl)-ethyl]-4-hydroxypiperidine-1-carboxylic acid benzyl ester | HCID 57458014 | — |
| Product | 5-(4-Fluorobenzyl)-3-oxo-1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid benzyl ester | HCID 67527407 | 19% |
Reaction Steps
The title compound was prepared from aminoalcohol 103NLS28 (303 mg, 0.81 mmol) according to literature procedures (Clark et al., J. Med. Chem. 26:855-861 (1983)), by acylation of the amino function with chloroacetylchloride, followed by halogen exchange with NaI and ring closure of the iodide derivative in presence of tert-butoxide. Purification of the crude product by silica gel column chromatography, eluting with a stepwise gradient of 0-100% ethyl acetate in n-heptane, afforded the title compound (64 mg, 19% overall yield) as a colourless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07727999B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-4ff04c5e94c1429fb6e2c8b432ea5d8a |
| Source note | uspto-grants-2010_06 |