HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → ethyl 4-{[(1S,4S)-4-isopropyl-4-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopent-2-en-1-yl]amino}-3-methoxypiperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl 3-methoxy-4-oxopiperidine-1-carboxylate | HCID 2724451 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (1S,4S)-4-isopropyl-4-(4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-ylcarbonyl)cyclopent-2-en-1-amine | HCID 68484653 | — |
| Product | ethyl 4-{[(1S,4S)-4-isopropyl-4-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopent-2-en-1-yl]amino}-3-methoxypiperidine-1-carboxylate | HCID 59263093 | — |
Reaction Steps
The title compound was prepared by taking ethyl 3-methoxy-4-oxopiperidine-1-carboxylate (148 mg, 0.000737 mol) in Methylene chloride (3 mL, 0.04 mol) and adding (1S,4S)-4-isopropyl-4-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopent-2-en-1-amine (0.31 g, 0.00081 mol;), Triethylamine (0.8 mL, 0.006 mol;) and Sodium triacetoxyborohydride (0.312 g, 0.00147 mol). The reaction was stirred overnight. The reaction was quenched with (20 mL) NaOH and extracted with (3×10 mL) CH2Cl2. The organic layers were collected, dried over MgSO4 and concentrated in vacuo. The crude was taken on to the next step as-is (410 mg, 98%). MS calculated for C28H40F3N5O4: (M+H) 568; found 568.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700624B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-0c7c566142d84bf080e2a75548c841c8 |
| Source note | uspto-grants-2010_04 |