HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 86634657, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 86634658 | HCID 86634658 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86634657 | HCID 86634657 | 65.1% |
Reaction Steps
To a mixture of tert-butyl [(3R)-1-(trans-2-hydroxycyclohexyl)pyrrolidin-3-yl]carbamate (0.70 g, 2.46 mmol) and 60% NaH (0.108 g, 2.71 mmol) in DMF (5 mL) at 0° C. was added benzyl bromide (0.79 mL, 2.71 mmol). After being stirred overnight under N2, water and EtOAc were added. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), concentrated and flash chromatographed (EtOAc to 10% MeOH/EtOAc) to give 0.60 g of the title compound. MS (EI) calcd: (M+H)+=375.3. Found: 375.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08362003B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-f71c8320d8ad4f2887124503af07dff3 |
| Source note | uspto-grants-2013_01 |