HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (R)-Cyclohexyl-[(3S,4S)-3-(4-imidazo[4,5-b]pyridin-3-yl-piperidin-1-ylmethyl)-4-phenyl-pyrrolidin-1-yl]-acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | 1-Piperidin-4-yl-5-fluoro-1-H-benzoimidazole | HCID 21193111 | — |
| Reactant | alpha-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid 4-methoxybenzyl ester | HCID 53654320 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-Cyclohexyl-[(3S,4S)-3-(4-imidazo[4,5-b]pyridin-3-yl-piperidin-1-ylmethyl)-4-phenyl-pyrrolidin-1-yl]-acetic acid | HCID 20664163 | — |
Reaction Steps
The title compound was prepared from 60 mg of α-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, 4-methoxy-benzyl ester (prepared above as Aldehyde 5), 60 mg 1-piperidin-4-yl-5-fluoro-1-H-benzoimidazole (from Step D ) and 75 mg of sodium triacetoxyborohydride in 4 mL of THF and 1 mL of DMF, using a procedure analogous to that described in Example 95, Step D to provide 48 mg of the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06248755B1 |
| Source dataset | uspto-grants-2001_06 |
| ORD ID | ord-c0f9602127ff4b0fb102bb5479b5dd8a |
| Source note | uspto-grants-2001_06 |