Water → HCID 19351096, compound

HRID 1636384Notes

Reaction equation

HRID 1636384 reaction equation
[CH:1]([N:4]1[CH:13]([C:14](O)=[O:15])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH:1]([N:4]1[CH:13]([CH2:14][OH:15])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 16243895HCID 16243895, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19351096HCID 19351096, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A sospension of N-isopropyl-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (8.0 g, 36 mmol) in tetrahydrofuran (100 ml) was slowly added to a refluxing suspension of lithium aluminum hydride (2.1 g, 54 mmol) in tetrahydrofuran (100 ml). The mixture was refluxed for two hours, then cooled at room temperature and treated with a mixture of tetrahydrofuran (7 ml) and water (0.9 ml), with 20% sodium hydroxide (2.3 ml) and finally with water (9.2 ml). The white solid was filtered off and the solvent was removed under reduced pressure yielding 5.0 g (yield 68%) of pure N-isopropyl-1,2,3,4-tetrahydroisoquinol-3-ylmethanol as thick oil. 1H-NMR δ7.12 (m, 4H), 4.54 (bs, 1H, exchange with D2O), 3.68 (s, 2H), 3.55-3.35 (m, 2H), 3.20-2.90 (m, 2H), 2.79 (d, 2H), 1.10 (d, 3H), 1.01 (d, 3H).

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. filtrationThe white solid was filtered off
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fcebf57d676840579b7e3787cda2e9e9
Source dataset
uspto-grants-2000_03
Patent number
US06034096

Reaction notes

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