HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzylamine → Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Ethyl(1S,2R,3S,6S)-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)-6-formylcyclohexanecarboxylate | HCID 86628113 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | Ethyl (1R,2R,3S,6S)-6-[(benzylamino)methyl]-3-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-2-(4-fluorophenyl)cyclohexanecarboxylate | HCID 86628114 | 97% |
Reaction Steps
A solution of aldehyde obtained from Step C (0.45 g, 0.84 mmol), benzyl amine (0.093 mL, 0.85 mmol), sodium triacetoxy borohydride (0.55 g, 2.6 mmol) in 30 mL dichloromethane was stirred at room temperature for 12 hr. The reaction mixture was washed with 2 N aq. NaOH, brine, dried over MgSO4, filtered and the solvent was removed under vacuum to give the title compound (0.51 g) which was used without further purification. MS: (MH)+ 626.6.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07683068B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-d2ebb5741dc04750a3703540432101cc |
| Source note | uspto-grants-2010_03 |