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

HRID 2383050노트

반응식

HRID 2383050 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a3547cb828a04d2caed2484a33e1fc11
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263607B2

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