N-Hydroxyphthalimide → 1-Acetyl-3,5-dimethyl Adamantane

HRID 2302099Notes

Reaction equation

HRID 2302099 reaction equation
[OH:1]N1[C:6](=[O:7])[C:5]2=CC=CC=C2C1=O.[C:13]([C:16]12[CH2:26][C:20]3([CH3:27])[CH2:21][C:22]([OH:25])([CH2:24][C:18]([CH3:28])([CH2:19]3)[CH2:17]1)[CH2:23]2)(=[O:15])[CH3:14]>>[C:13]([C:16]12[CH2:26][C:20]3([CH3:27])[CH2:21][CH:22]([CH2:24][C:18]([CH3:28])([CH2:19]3)[CH2:17]1)[CH2:23]2)(=[O:15])[CH3:14].[C:13]([C:16]12[CH2:26][C:20]3([CH3:27])[CH2:19][C:18]([CH3:28])([CH2:24][C:22]([C:6](=[O:7])[CH3:5])([CH2:21]3)[CH2:23]1)[CH2:17]2)(=[O:15])[CH3:14].[CH3:13][C:16]12[CH2:23][C:22]3([OH:25])[CH2:24][CH:18]([CH2:19][C:20]([CH3:27])([CH2:21]3)[CH2:26]1)[CH2:17]2.[CH3:27][C:20]12[CH2:21][CH:22]3[CH2:23][CH:16]([CH2:17][C:18]([CH3:28])([C:24]3=[O:1])[CH2:19]1)[CH2:26]2

Participants

6

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 134640741-Acetyl-3,5-dimethyl-7-adamantanol

Product 4

HCID 2657933,5-Dimethyl-1-adamantanolYield 7%HCID 121131241-Acetyl-3,5-dimethyl AdamantaneYield 32%HCID 121131411,3-Diacetyl-5,7-dimethyladamantaneYield 2%HCID 126443321,3-Dimethyl-4-adamantanoneYield 5%

Procedure

Except that the amount of N-hydroxyphthalimide was changed to 0.6 mmol, the procedure of Example 9 was repeated to give 1-acetyl-3,5-dimethyladamantane (yield 32%, selectivity 54%), 1,3-diacetyl-5,7-dimethyladamantane (yield 2%, selectivity 3%), 1-acetyl-3,5-dimethyl-7-adamantanol (yield %, selectivity 2%), 1,3-dimethyl-5-adamantanol (yield 7%, selectivity 12%), and 1,3-dimethyl-4-adamantanone (yield 5%, selectivity 8%), at a conversion rate from 1,3-dimethyladamantane of 59%.

Sources & evidence

ORD record
ord-7d1ff4c668d94946a51b76cdc3322555
Source dataset
uspto-grants-2002_08
Patent number
US06429314B1

Reaction notes

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