Benzaldehyde → Ethyl 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

HRID 2383050ノート

反応式

HRID 2383050 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[CH:16]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][NH:17]1.[CH:31](=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[OH-].[Na+]>C(O)(=O)C>[CH2:31]([N:17]1[CH2:18][CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]1[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 44890894Ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate--hydrogen chloride (1/1)

生成物 1

HCID 59396192Ethyl 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate収率 32.7%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

In an ice bath, sodium triacetoxyborohydride (6.11 g) was added to a solution of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate hydrochloride (4.98 g) and benzaldehyde (2.72 g) in acetic acid (50 mL). The mixture was stirred at room temperature for 15 hours. A 1 M aqueous NaOH solution was added to the reaction liquid which was then extracted with chloroform. The extract was washed with water and saturated brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain ethyl 2-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate (1.99 g).

後処理

  1. extractionwas then extracted with chloroform
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

出典と根拠

ORDレコード
ord-a3547cb828a04d2caed2484a33e1fc11
出典データセット
uspto-grants-2012_09
特許番号
US08263607B2

反応ノート

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