Hydrochloric Acid → 4-(4-Hydroxy-4-tert-butylbenzylcyclohexylamino)-3-methoxy-2-methylpyridine

HRID 1008

反応式

HRID 1008 の反応式
[Mg].[C:2]([C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].O=[C:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[C:23]=2[O:29][CH3:30])[CH2:17][CH2:16]1.Cl.C1C[O:35]CC1>CCOCC>[OH:35][C:6]1([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:13]=[CH:12][C:9]([CH2:10][N:21]([CH:18]2[CH2:19][CH2:20][CH2:15][CH2:16][CH2:17]2)[C:22]2[CH:27]=[CH:26][N:25]=[C:24]([CH3:28])[C:23]=2[O:29][CH3:30])=[CH:8][CH2:7]1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 5462224MagnesiumHCID 196939514-(4-Oxocyclohexylamino)-3-methoxy-2-methylpyridine

生成物 1

HCID 676711404-(4-Hydroxy-4-tert-butylbenzylcyclohexylamino)-3-methoxy-2-methylpyridine

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A Grignard solution is prepared from 1.2 g of magnesium and 12.9 g of 90% strength 4-tert-butylbenzyl bromide in 100 ml of abs. ether. 2.9 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine in 50 ml of absolute THF are added dropwise to this solution. After 17 hours at room temperature it is acidified with 25 ml of 2N HCl, the mixture is extracted several times with ethyl acetate and the combined ethyl acetate phases are washed with sodium hydrogen carbonate solution. Purification is carried out by column chromatography on silica gel using ethyl acetate to which increasing amounts of methanol are added.

後処理

  1. extractionthe mixture is extracted several times with ethyl acetate
  2. washthe combined ethyl acetate phases are washed with sodium hydrogen carbonate solution
  3. customPurification
  4. temperatureincreasing amounts of methanol
  5. additionare added

出典と根拠

ORDレコード
ord-77b579259b0e47c2ac2dc691717deb93
出典データセット
uspto-grants-1998_03
特許番号
US05723450

関連ノート

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