Dichloromethane → (R)-{2-[1-(4-Bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl methyl]-1,2,3,4-tetrahydro-isoquinolin-3-yl}-methanol

HRID 1740103ノート

反応式

HRID 1740103 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]([CH2:14][CH3:15])=[C:12]([CH2:16]O)[C:11]([CH2:18][CH3:19])=[N:10]2)=[C:4]([CH3:20])[CH:3]=1.C(N(CC)CC)C.C(Cl)Cl.[OH:31][CH2:32][CH:33]1[CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35][NH:34]1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]([CH2:14][CH3:15])=[C:12]([CH2:16][N:34]3[C@@H:33]([CH2:32][OH:31])[CH2:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:35]3)[C:11]([CH2:18][CH3:19])=[N:10]2)=[C:4]([CH3:20])[CH:3]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 3752277(1,2,3,4-Tetrahydro-isoquinolin-3-yl)-methanolHCID 218373201-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl-methanol

生成物 1

HCID 54272289(R)-{2-[1-(4-Bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl methyl]-1,2,3,4-tetrahydro-isoquinolin-3-yl}-methanol収率 135.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To an ice bath-chilled solution of [1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl-methanol (770 mg, 2.3 mmol) and triethylamine (0.382 ml, 2.7 mmol) in methylene chloride (10 ml) methane sulfonyl chloride (0.1 94 ml, 2.5 mmol) was added dropwise. After stirring the reaction at 0-5° C. for 30 minutes, (+)-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (1.49 g, 9.1 mmol) and anhydrous N,N-dimethylformamide (2.2 ml) were added, and the resulting reaction mixture was heated (50° C. oil bath) for 21 hours. The solvent was removed in vacuo, and the residue was extracted with ethyl acetate/water (10 ml of each). The aqueous phase was then extracted twice with equal-volume portions of fresh ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to afford a yellow oil (1.5 g). Flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:5 in volume) afforded the title compound (0.45 g) as a light yellow oil.

後処理

  1. customthe reaction at 0-5° C. for 30 minutes
  2. customthe resulting reaction mixture
  3. customThe solvent was removed in vacuo
  4. extractionthe residue was extracted with ethyl acetate/water (10 ml of each)
  5. extractionThe aqueous phase was then extracted twice with equal-volume portions of fresh ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3bdcaf4d63104304b3be77c91c479f14
出典データセット
uspto-grants-1999_10
特許番号
US05968944

反応ノート

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