2-(Naphthalen-1-yl)acetyl chloride → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2methoxyphenyl)-2-[(1-naphthyl)acetyl]perhydro-4,5-isoindolediol

HRID 1780971Notes

Reaction equation

HRID 1780971 reaction equation
[C:1]1([C:7]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:15]3[CH:11]([CH2:12][NH:13][CH2:14]3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])([OH:16])[CH:9]([OH:25])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:32]1([CH2:42][C:43](Cl)=[O:44])[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1>>[C:26]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:15]3[CH:11]([CH2:12][N:13]([C:43](=[O:44])[CH2:42][C:32]4[C:41]5[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=5)[CH:35]=[CH:34][CH:33]=4)[CH2:14]3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH3:24])([OH:16])[CH:9]([OH:25])[CH2:8]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 27953862-(Naphthalen-1-yl)acetyl chlorideHCID 19047650(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol

Product 1

HCID 67719299(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2methoxyphenyl)-2-[(1-naphthyl)acetyl]perhydro-4,5-isoindolediolYield 45.9%

Procedure

By working according to the procedure of Example A, starting from 0.62 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydro-4,5-isoindolediol and 0.35 g of 1-naphthylacetyl chloride, 0.4 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2methoxyphenyl)-2-[(1-naphthyl)acetyl]perhydro-4,5-isoindolediol is obtained, melting at 188°-190° C.

Sources & evidence

ORD record
ord-f702a20ae3d74a158601fb61cb6aa32b
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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