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

HRID 2383050Notes

Reaction equation

HRID 2383050 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a3547cb828a04d2caed2484a33e1fc11
Source dataset
uspto-grants-2012_09
Patent number
US08263607B2

Reaction notes

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