HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Ethylphenyl isocyanate → (2S,4R)-tert-butyl 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-((4-ethylphenylcarbamoyloxy)methyl)pyrrolidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Ethylphenyl isocyanate | HCID 90007 | — |
| Reactant | (2S,4R)-tert-butyl 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(hydroxymethyl)pyrrolidine-1-carboxylate | HCID 59778629 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2S,4R)-tert-butyl 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-((4-ethylphenylcarbamoyloxy)methyl)pyrrolidine-1-carboxylate | HCID 59778440 | — |
Reaction Steps
To a solution of (2S,4R)-tert-butyl 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (403 mg, 0.92 mmol) and DMAP (134 mg, 1.1 mmol) in THF (10 mL) was added 4-ethylphenyl isocyanate (162 mg, 11 mmol). The reaction mixture was stirred at rt overnight and concentrated to give (2S,4R)-tert-butyl 4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-((4-ethylphenylcarbamoyloxy)methyl)pyrrolidine-1-carboxylate, which was used without further purification. LRMS (M+H+) m/z 585.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071625B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-cb8da034f9624745a209c1c6d9486106 |
| Source note | uspto-grants-2011_12 |