HuagongsheHuagongshe Chemistry Print Report · For research reference only
Heptane → 1-cyclopentyl N-[2-(1-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-leucinate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Heptane | HCID 8900 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | L-leucine cyclopentyl ester tosylate | HCID 86633653 | — |
| Reactant | 2-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehyde | HCID 86686420 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | 1-cyclopentyl N-[2-(1-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-leucinate | HCID 86686419 | 75% |
Reaction Steps
To a solution of Intermediate D (0.245 g, 0.5 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (0.398 g, 1.07 mmol) and sodium triacetoxyborohydride (0.417 g, 1.97 mmol). The mixture was stirred for one hour then loaded directly onto a silica gel column and eluted with 7:3 ethyl acetate:heptane to yield the desired product (0.250 g, 75% yield). LC/MS: m/z 667.25 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321718B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-45f7d73041424261baf06287d757f1e0 |
| Source note | uspto-grants-2016_04 |