Sodium borohydride → 6-Methoxy-1-thiophen-2-yl-1,2,3,4-tetrahydroisoquinoline

HRID 397051Notes

Reaction equation

HRID 397051 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[N:10][CH2:9][CH2:8]2>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[NH:10][CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 108002866-Methoxy-1-thiophen-2-yl-3,4-dihydroisoquinoline

Product 1

HCID 51632326-Methoxy-1-thiophen-2-yl-1,2,3,4-tetrahydroisoquinolineYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.916 g, 24.2 mmol) was added in small portions to a solution of 6-methoxy-1-thiophen-2-yl-3,4-dihydroisoquinoline (1.470 g, 6.04 mmol) in MeOH (50 ml) at 0° C. The reaction mixture was stirred for 30 min, warmed to rt and stirred at rt for 21 hr, then quenched by the dropwise addition of H2O (10 ml). Excess MeOH was removed by evaporation and the resulting aqueous solution was extracted with CHCl3 (4×10 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 1.316 g (89% yield) of yellow solid.

Workup

  1. stirringstirred at rt for 21 hr
  2. customquenched by the dropwise addition of H2O (10 ml)
  3. customExcess MeOH was removed by evaporation
  4. extractionthe resulting aqueous solution was extracted with CHCl3 (4×10 ml)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-512fec893adc4ee89ba59f9e1add20a5
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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