3-Thiophenacetic acid → (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(3-thienyl)acetyl]perhydroisoindol-4-ol

HRID 375436Notes

Reaction equation

HRID 375436 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.[S:32]1[CH:36]=[CH:35][C:34]([CH2:37][C:38](O)=[O:39])=[CH:33]1>>[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:38](=[O:39])[CH2:37][C:34]4[CH:35]=[CH:36][S:32][CH:33]=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 234043-Thiophenacetic acidHCID 70218598(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride

Product 1

HCID 57043806(3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(3-thienyl)acetyl]perhydroisoindol-4-olYield 55.2%

Procedure

By working in accordance with Example 4, starting from 0.8 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindol-4-ol hydrochloride and 0.34 g of 3-thienylacetic acid, 0.53 g of (3aS,4S,7aS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-[(3-thienyl)acetyl]perhydroisoindol-4-ol is obtained in the form of white crystals which melt with decomposition at 106° C.

Sources & evidence

ORD record
ord-ff34104ce16846aca9f8af9ad2b98ba2
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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