Aluminium lithium hydride → 5-(Benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 717367Notes

Reaction equation

HRID 717367 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][C:14]2=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:18]([O:19][CH3:20])=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][NH:13][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90411434HCID 90411434, compound

Product 1

HCID 214470265-(Benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 50-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinolin-1-one (1 g, 3.53 mmol, 1.00 equiv), oxolane (20 mL) and LiAlH4 (400 mg, 11.79 mmol, 3.00 equiv). The resulting solution was heated to reflux for 2 hr. The reaction mixture was cooled to 0° C. with a water/ice bath. The reaction was then quenched by the addition of 0.4 mL of water. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 0.8 g (crude) of 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline as light yellow oil. MS (ESI) m/z 270 ([M+H]+).

Workup

  1. customInto a 50-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 2 hr
  5. customThe reaction was then quenched by the addition of 0.4 mL of water
  6. filtrationThe solids were filtered out
  7. concentrationThe resulting mixture was concentrated under vacuum
  8. customThis resulted in 0.8 g (crude) of 5-(benzyloxy)-6-methoxy-1,2,3,4-tetrahydroisoquinoline as light yellow oil

Sources & evidence

ORD record
ord-bcfa11a35a8c442e81a3062d7bab688b
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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