HuagongsheHuagongshe Chemistry Print Report · For research reference only
(4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol → (4bS,8R,8aR,9aR,10S,13aR,13bR)-7-allyl-10-tert-butyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (4bS,8R,8aS,9aR,10S,13aR,13bR)-10-tert-butyl-7-cyclopropylmethyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol | HCID 73211769 | — |
| Reactant | 17-cyclopropylmethyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinan | HCID 86711659 | — |
| Reactant | 17-allyl-7alpha-[(2S)-3,3-dimethyl-2-hydroxybutan-2-yl]-4,5alpha-epoxy-3,6-dihydroxy-6alpha,14alpha-ethanomorphinan | HCID 86711663 | — |
| Product | (4bS,8R,8aR,9aR,10S,13aR,13bR)-7-allyl-10-tert-butyl-5,6,7,8,9,9a,10,13b-octahydro-10-methyl-8a,13a-ethano-4,8-methanobenzofuro[3,2-e][1,3]dioxino[4,5-g]isoquinolin-1-ol | HCID 86711664 | 49% |
Reaction Steps
The title compound 17 was synthesized similar to the procedure described in Example 1 for preparing compound 3 using compound 16 rather than compound 2. After column chromatography, 1.29 g (49.0% yield) of compound 17 was isolated in a purity of >99% as a-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09315514B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-6ec913134b814e89a44410f7a60fc59e |
| Source note | uspto-grants-2016_04 |