Dimethylamine → 1-(N,N-dimethylcarbamoyl)-3-methoxycarbonyladamantane

HRID 992164Notes

Reaction equation

HRID 992164 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][O:5][C:6]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18]([O:20]C)=O)([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:7]>C1COCC1>[CH3:4][O:5][C:6]([C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([C:18](=[O:20])[N:2]([CH3:3])[CH3:1])([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:7]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 365223Dimethyl 1,3-adamantanedicarboxylate

Product 1

HCID 184104771-(N,N-dimethylcarbamoyl)-3-methoxycarbonyladamantaneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 mmole of 1,3-bis(methozxycarbonyl)adamantane obtained by the method of Example 84 was dissolved in 30 ml of THF. To the mixture, 0.5 mmole of dimethylamine and 0.1 mmole of aluminum chloride anhydride AlCl3 was added and reacted for 6 hours at 80° C. As a result, The conversion of 1,3-bis(methoxycarbonyl)adamantane was 90%, and 1-methoxycarbonyl-3-(N,N-dimethylcarbamoyl)adamantane (yield 80%) was formed.

Workup

  1. customreacted for 6 hours at 80° C

Sources & evidence

ORD record
ord-412942a19b374c38be373ab763298900
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Reaction notes

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