Sodium triacetoxyborohydride → 7-Bromo-2-(1-(4-cyanobenzyl)-5-imidazolylmethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1601027Notes

Reaction equation

HRID 1601027 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:27]=[CH:26][C:17]([CH2:18][N:19]2[C:23]([CH:24]=O)=[CH:22][N:21]=[CH:20]2)=[CH:16][CH:15]=1)#[N:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(C(Cl)Cl)(Cl)Cl.CCOC(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:24][C:23]3[N:19]([CH2:18][C:17]4[CH:26]=[CH:27][C:14]([C:12]#[N:13])=[CH:15][CH:16]=4)[CH:20]=[N:21][CH:22]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydride2×HCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 107292557-Bromo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 98660807-Bromo-2-(1-(4-cyanobenzyl)-5-imidazolylmethyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 65911,1,2,2-TetrachloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-bromo-1,2,3,4-tetrahydroisoquinoline (0.742 g, 3.5 mmol) in CHCl2CHCl2 (15 mL) was added 1-(4-cyanobenzyl)-5-imidazole carboxaldehyde (0.812 g, 3.85 mmol), 4 Å sieves and NaBH(OAc)3 (1.11 g, 5.25 mmol). The mixture was stirred at room temperature for 16 h. and a further portion of NaBH(OAc)3 (0.55 g, 2.6 mmol) was added. After an additional 24 h the mixture was diluted with EtOAc, filtered through celite, washed with brine, dried (Na2SO4) and concentrated. The residue was stirred in 2N Hcl (50 mL) for 2 h. then extracted with ether. The aqueous layer was basified with 6N KOH and extracted 3× CH2Cl2 which was then washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. Crystallization from ether afforded the title compound as a white solid.

Workup

  1. filtrationfiltered through celite
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. stirringThe residue was stirred in 2N Hcl (50 mL) for 2 h.
  6. extractionthen extracted with ether
  7. extractionextracted 3× CH2Cl2 which
  8. washwas then washed with brine
  9. dry with materialdried (Na2SO4)
  10. customthe solvent evaporated in vacuo
  11. customCrystallization from ether

Sources & evidence

ORD record
ord-7b67745e3ea741c88889f1d8462fafc0
Source dataset
uspto-grants-1999_11
Patent number
US05977134

Reaction notes

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