HCID 19610221, compound → HCID 19610234, compound

HRID 1602179Notes

Reaction equation

HRID 1602179 reaction equation
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH:4]([C:14](OC)=[O:15])[NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH2:5][CH:4]([CH2:14][OH:15])[NH:3]1

Participants

4

Reactant 2

HCID 19610221HCID 19610221, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19610234HCID 19610234, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydro-1-methyl-3-methoxycarbonyl-7-methoxyisoquinoline (0.67 g, 2.87 mmol) (described in example 73) in anhydrous tetrahydrofuran (5 mnL) was added dropwise I M solution of lithium aluminium hydride (5.7 nunol) in anhydrous tetrahydrofuran (5.7 mL). The mixture was stirred at rt for 3 hr. The reaction mixture was quenched by a careful addition of 5N NaOH (2 mL). The mixture was stirred at room temperature for 10 min and then filtered and the solid was washed twice with diethylether. The organic filtrates were combined, dried (MgSO4) and concentrated in vacuo to give the desired product as solid foam (0.486 g, 82%): 1H-NMR (CDCl3, δ) 1.48 (d,J=6.31Hz, 3H), 2.46-2.67 (m, 2H), 3.04-3.12 (m, 1H), 3.72 (dd, J=8.4, 11.1 Hz, 1H), 3.72-3.81 (m, 1H), 3.79 (s, 3H), 4.08 (q. J=6.3 Hz, 1H), 6.71-6.75 (m, 2H), 7.02 (d, J =7.8 Hz, 1H): MS showed (M+H) +@ 208.

Workup

  1. customThe reaction mixture was quenched by a careful addition of 5N NaOH (2 mL)
  2. stirringThe mixture was stirred at room temperature for 10 min
  3. filtrationfiltered
  4. washthe solid was washed twice with diethylether
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-11e81d8369404755bf95212d807be51c
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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