HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane → tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane | HCID 9923113 | — |
| Reactant | Tert-butyl 3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-oxopropylcarbamate | HCID 68524283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate | HCID 86641455 | — |
Reaction Steps
A mixture of tert-butyl 3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-oxopropylcarbamate and (+)-Ipc2BCl in anhydrous THF is stirred at room temperature until no starting material is seen by TLC. The reaction is then quenched with aqueous NH4Cl and stirred at room temperature. Extraction with EtOAc and drying over anhydrous MgSO4 followed by flash chromatography (EtOAc—hexanes gradient) gives tert-butyl (R)-3-(3-(tert-butoxycarbonyl(cyclohexylmethyl)amino)phenyl)-3-hydroxypropylcarbamate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08674137B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-dafcf108c24d41ca90094491f341e634 |
| Source note | uspto-grants-2014_03 |