反応式
Cl.[NH2:2][C@@H:3]1CCCC[C@H:4]1[NH2:9].C([C:14]1[C:15]([OH:26])=[C:16]([CH:19]=[C:20](C(C)(C)C)[CH:21]=1)[CH:17]=O)(C)(C)C.C(C1C=CC([C:35]2[C:36]([OH:47])=[C:37]([CH:40]=[C:41](C(C)(C)C)[CH:42]=2)[CH:38]=O)=CC=1)=C.C(N(CC)CC)C>ClCCl.C(O)C.CO>[CH:20]1[CH:21]=[CH:14][C:15](=[O:26])/[C:16](=[CH:17]\[NH:2][CH2:3][CH2:4][NH:9]/[CH:38]=[C:37]2\[C:36]([CH:35]=[CH:42][CH:41]=[CH:40]\2)=[O:47])/[CH:19]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
実験手順
To a 500 mL flask was charged with (1R,2R)-1,2-diaminocyclohexane monohydrochloride salt (1.51 g, 10 mmol), activated 4 A molecular sieve (4.0 g), anhydrous methanol (40 mL) and ethanol (40 mL). 3,5-Di-t-butyl-2-hydroxybenzaldehyde (2.34 g, 10 mmol) was added in one portion and the reaction mixture was stirred at rt for 4 h. TLC showed that all the aldehyde was consumed. A solution of 3-(4′-vinylphenyl)-5-t-butyl-2-hydroxybenzaldehyde (2.74 g, 10 mmol) in dichloromethane (80 mL) was added to reaction system, followed by the addition of triethylamine (2.8 mL, 20 mmol) in a dropwise fashion. After the reaction mixture was stirred at rt for additional 4 h, all the solvents were removed by rotovap. The residue was dissolved in dichloromethane (100 mL), washed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL), and dried with magnesium sulfate. The desired compound 1 (5.05 g, 85.2%) was isolated by flash chromatography of the crude product with 1/50 ether/hexanes.
後処理
- customwas consumed
- stirringAfter the reaction mixture was stirred at rt for additional 4 h
- customall the solvents were removed by rotovap
- dissolutionThe residue was dissolved in dichloromethane (100 mL)
- washwashed with aqueous hydrochloric acid (1 M, 50 mL) and water (2×50 mL)
- dry with materialdried with magnesium sulfate
出典と根拠
- ORDレコード
- ord-144365a3c2074308b5f80ea608055380
- 出典データセット
- uspto-grants-2012_06
- 特許番号
- US08207365B2
関連ノート
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