HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phthalimide → tert-butyl {(1S)-2-cyclohexyl-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phthalimide | HCID 6809 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | (S)-(-)-2-(tert-Butoxycarbonylamino)-3-cyclohexyl-1-propanol | HCID 11043405 | — |
| Product | tert-butyl {(1S)-2-cyclohexyl-1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]ethyl}carbamate | HCID 57544826 | 56% |
Reaction Steps
A mixture of tert-butyl[(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate (3.3 g, 13 mmol), phthalimide (2.10 g, 14.3 mmol), triphenylphosphine (3.75 g, 14.3 mmol), diisopropyl azodicarboxylate (3.58 mL, 18.2 mmol) in tetrahydrofuran (30 mL, 400 mmol) was stirred at room temperature overnight. Direct purification by combi-flash chromatography afforded 2.8 g (56% yield) of the desired product. LC-MS found: 287.1 (M−Boc)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08895571B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-e9a59f37e767480391c914f5f721919e |
| Source note | uspto-grants-2014_11 |