HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-isopropenyl-1'-(3-piperidin-1-yl-propyl) spiro[3H-indole-3,3' piperidine]-2,6'(1H)-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | (2'R,3R,4'S)-6-chloro-4'-(3-chloro-phenyl)-1'-(3-chloro-propyl)-2'-isopropenyl-2,3-dihydro-2,6'-dioxospiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane | HCID 68958092 | — |
| Product | Diisopropylethylamine | HCID 81531 | — |
| Product | racemic (2'R,3R,4'S)-6-chloro-4'-(3-chlorophenyl)-2'-isopropenyl-1'-(3-piperidin-1-yl-propyl) spiro[3H-indole-3,3' piperidine]-2,6'(1H)-dione | HCID 76568019 | 23.1% |
Reaction Steps
In a manner similar to the method described in example 60b, (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-1′-(3-chloro-propyl)-2′-isopropenyl-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane prepared in example 123a (0.12 g, 0.20 mmol) was reacted with piperidine (2 mL), trifluoroacetic acid (1 mL) and then N,N′-diisopropylethylamine (1.5 mL) to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-isopropenyl-1′-(3-piperidin-1-yl-propyl)spiro[3H-indole-3,3′ piperidine]-2,6′(1H)-dione as a yellow solid (Yield: 40 mg, 23.1%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07495007B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-556b050a8e9742b6ab4e5aa3b28fd39a |
| Source note | uspto-grants-2009_02 |