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

HRID 1937239Notes

Reaction equation

HRID 1937239 reaction equation
C([C:4]12[CH2:13][C:8]3(O)[CH2:9][CH:10]([CH2:12][C:6]([C:15]([OH:17])=[O:16])([CH2:7]3)[CH2:5]1)[CH2:11]2)(O)=O.N.[C:19](C12CC3(O)CC(O)(CC(C(O)=O)(C3)C1)C2)(O)=O.NN.N(C(C12CC3(O)CC(O)(CC(C(NN)=O)(C3)C1)C2)=O)N.[CH3:59][N:60]([CH3:74])[C:61](C12CC3CC(CC(O)(C3)C1)C2)=[O:62].[Cl-].CNC>>[CH3:59][N:60]([CH3:74])[C:61]([C:8]12[CH2:13][CH:4]3[CH2:11][CH:10]([CH2:12][C:6]([C:15]([O:17][CH3:19])=[O:16])([CH2:5]3)[CH2:7]1)[CH2:9]2)=[O:62]

Participants

9

Reactant 8

HCID 222AmmoniaHCID 312ChlorideHCID 674DimethylamineHCID 9321HydrazineHCID 120106445-Hydroxy-1,3-adamantanedicarboxylic acidHCID 120704631,3-Dicarboxy-5,7-adamantanediolHCID 120704711-(N,N-dimethylcarbamoyl)-3-adamantanolHCID 177806841,3-Di(hydrazinocarbonyl)-5,7-adamantanediol

Product 1

HCID 184104771-(N,N-dimethylcarbamoyl)-3-methoxycarbonyladamantane

Procedure

For example, reaction of 1,3-dicarboxy-5-adamantanol with ammonia provides 1,3-dicarbamoyl-5-admatanol. Reaction of 1,3-dicarboxy-5,7-adamantanediol with hydrazine forms 1, 3-di(hydrazinocarbonyl)-5,7-adamantanediol, etc. 1-(N, N-dimethylcarbamoyl)-3-adamantanol can be obtained by acting thyonyl chloride on 1-carboxy-3-adamantanol followed by reacting the resultant compound with dimethylamine. Similarly, 1-(N,N-dimethylcarbamoyl)-3-methoxycarbonyladamantane can be formed from 1-carboxy-3-methoxycarbonyladamatane,

Workup

  1. customprovides 1,3-dicarbamoyl-5-admatanol
  2. customcan be obtained

Sources & evidence

ORD record
ord-fec9ebdf20f14026916ff8913e9aa418
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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