Sodium Acetate → 2-(4-Imidazol-1-yl-benzyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

HRID 397088Notes

Reaction equation

HRID 397088 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[C:24]4[C:19](=[CH:20][C:21]([OH:25])=[CH:22][CH:23]=4)[CH2:18][CH2:17][NH:16]3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:26]1([C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)[CH:30]=[CH:29][N:28]=[CH:27]1.CC([O-])=O.[Na+].C([BH3-])#N.[Na+]>CO>[N:26]1([C:31]2[CH:38]=[CH:37][C:34]([CH2:35][N:16]3[CH2:17][CH2:18][C:19]4[C:24](=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=4)[CH:15]3[C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[CH:10][CH:11]=3)=[CH:33][CH:32]=2)[CH:30]=[CH:29][N:28]=[CH:27]1

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 7365304-(1H-imidazol-1-yl)benzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 181724491-[4-(2-Pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol

Product 1

HCID 181723912-(4-Imidazol-1-yl-benzyl)-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-olYield 112.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinolin-6-ol (0.023 g, 0.067 mmol), 4-imidazol-1-yl-benzaldehyde (0.011 g, 0.063 mmol), NaOAc (0.011 g, 0.14 mmol), and sodium cyanoborohydride (0.004 g, 0.063 mmol) in MeOH (2.0 ml) was stirred at rt for 18 hr. The reaction mixture was evaporated in vacuo to a yellow residue that was dissolved in EtOAc (5 ml) and washed first with sat. NaHCO3 solution (5 ml) and then with H2O (5 ml). The organic solution was dried over MgSO4 and evaporated to give 0.035 g of yellow residue. Purification by preparative TLC, eluting with EtOAc:MeOH (7:3), gave 0.007 g (23% yield) of white solid.

Workup

  1. customThe reaction mixture was evaporated in vacuo to a yellow residue that
  2. dissolutionwas dissolved in EtOAc (5 ml)
  3. washwashed first with sat. NaHCO3 solution (5 ml)
  4. dry with materialThe organic solution was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-ca3227ff177140879ce3c5041d487307
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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