HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-(TrifluoroMethoxy)phenyl isocyanate → (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-(TrifluoroMethoxy)phenyl isocyanate | HCID 20067555 | — |
| Reactant | (4S)-6-Azaspiro[2.5]octan-4-ol | HCID 44541813 | — |
| Reactant | (S)-4-[(S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-5-methoxy-pentanoic acid | HCID 67074561 | — |
| Solvent | Isopropanol heptane | HCID 21225753 | — |
| Product | (4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride | HCID 44541812 | — |
| Product | (S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-1-[(S)-4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-methoxymethyl-4-oxo-butyl]-3-methyl-piperazin-2-one | HCID 58232129 | — |
Reaction Steps
In analogy to intermediate 15, (S)-4-[(S)-4-(3-chloro-4-trifluoromethyl-phenyl)-3-methyl-2-oxo-piperazin-1-yl]-5-methoxy-pentanoic acid (61% ds) (intermediate 45) and 1.1 eq. of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2) gave after flash chromatography (SiO2, n-heptane/isopropanol 1:1) the titled compound in 30% yield (90% ds) as off-white waxy solid. MS: 532.22 (MH+, 1Cl).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08445674B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-457f8e9281a445b4bc55ddfb8083d783 |
| Source note | uspto-grants-2013_05 |