5-Fluoroindole-3-acetic acid → (3aS,4S,7aS)-7,7-diphenyl-2-[(5-fluoro-3-indolyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol

HRID 375439Notes

Reaction equation

HRID 375439 reaction equation
Cl.[C:2]1([C:8]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:16]3[C@@H:12]([CH2:13][NH:14][CH2:15]3)[C@@:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][CH:41]=1)[NH:38][CH:37]=[C:36]2[CH2:42][C:43](O)=[O:44]>>[C:26]1([C:8]2([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@@H:16]3[C@@H:12]([CH2:13][N:14]([C:43](=[O:44])[CH2:42][C:36]4[C:35]5[C:39](=[CH:40][CH:41]=[C:33]([F:32])[CH:34]=5)[NH:38][CH:37]=4)[CH2:15]3)[C@@:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])([OH:17])[CH2:10][CH2:9]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 967505-Fluoroindole-3-acetic acidHCID 70218598(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

Product 1

HCID 57167195(3aS,4S,7aS)-7,7-diphenyl-2-[(5-fluoro-3-indolyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-olYield 34.1%

Procedure

By working in accordance with the operating method of Example 4, starting from 0.8 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride and 0.39 g of (5-fluoro-3-indolyl)acetic acid, 0.36 g of (3aS,4S,7aS)-7,7-diphenyl-2-[(5-fluoro-3-indolyl)acetyl]-4-(2-methoxyphenyl)perhydroisoindol-4-ol is obtained in the form of white crystals which melt with decomposition at 170° C.

Sources & evidence

ORD record
ord-a1ddaaea3e874fcba24b6cc92f6c39fe
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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