N,N,N',N'-Tetramethylethylenediamine → 3-Methoxyphenyl-(2-hydroxy-2-adamantyl)-1-imidazolylmethane

HRID 1493737Notes

Reaction equation

C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=1)[CH2:11]N1C=CN=C1.C[N:21]([CH2:23][CH2:24][N:25]([CH3:27])C)C.[CH:28]12[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[C:29]1=[O:38])[CH2:35]2>CCCCCC.C1COCC1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:11]([C:29]2([OH:38])[CH:30]3[CH2:36][CH:34]4[CH2:33][CH:32]([CH2:37][CH:28]2[CH2:35]4)[CH2:31]3)[C:27]2[NH:25][CH:24]=[CH:23][N:21]=2)[CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -70 °C

Procedure

55 ml (85 mmol) of a 1.55 molar solution of n-butyllithium in hexane were added dropwise to a solution of 7.52 g (40 mmol) of N-(3-methoxybenzyl)-imidazole and 4.65 g (40 mmol) of TMEDA in 90 ml of absolute THF at -70° C. The mixture was stirred for a further 20 minutes at -70° C., and a solution of 6.01 g (40 mmol) of adamantanone in 30 ml of absolute THF was then added dropwise at -70° C. in the course of about 10 minutes. The procedure was then continued as described in Example 100. The residue (13 g) from the CH2Cl2 extract was crystallized from acetonitrile. 7.5 g of pure 3-methoxyphenyl-(2-hydroxy-2-adamantyl)-1-imidazolylmethane of melting point 182° C. were obtained.

Workup

extractionThe residue (13 g) from the CH2Cl2 extract
customwas crystallized from acetonitrile

Sources & evidence

ORD record: ord-c601cd9b36484a9fa2f8cac2b1f78b94
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05023357

Reaction notes

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