HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → N-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide | HCID 11155721 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N-(4-{1-Ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide | HCID 11477062 | 60.1% |
Reaction Steps
To a 0° C. mixture of N-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-N-methyl-methanesulfonamide (100 mg, 0.21 mmol), MeOH (5 mL), and THF (10 mL) is added NaBH4 (12 mg, 0.32 mmol). The reaction is warmed to RT and stirred for 5 h and concentrated. The residue is partitioned between EtOAc and 0.2 N HCl. The organic phase is Na2SO4 dried, concentrated, and chromatographed (0% to 25% EtOAc/Hex) to give the title compound (60 mg, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07750184B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-7ecc3cabfd684b07aca250fdd67bcdd7 |
| Source note | uspto-grants-2010_07 |