Water → (5,6,7,8-Tetrahydroisoquinolin-3-yl)methanol

HRID 1943158Notes

Reaction equation

HRID 1943158 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11](OCC)=[O:12])[N:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([CH2:11][OH:12])[N:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12384001Ethyl 5,6,7,8-tetrahydro-3-isoquinolinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18799805(5,6,7,8-Tetrahydroisoquinolin-3-yl)methanolYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5,6,7,8-tetrahydro-3-isoquinolinecarboxylate (1.27 g, 6.19 mmol) in THF (50 ml) at −78° C. under argon was treated with LiAlH4 (1M solution in THF, 6.19 ml, 6.19 mmol) and allowed warm to rt. After 10 min at rt, water (1 ml), 2M aq NaOH (1 ml) and water (1 ml) were sequentially added and the mixture stirred at rt for 0.5 h. The mixture was then filtered through a short pad of Kieselguhr, eluting with THF (50 ml), organic extracts were then evaporated, chromatographed (0-20% methanol/DCM) to give product as an orange oil (0.572 g, 57%).

Workup

  1. filtrationThe mixture was then filtered through a short pad of Kieselguhr
  2. washeluting with THF (50 ml), organic extracts
  3. customwere then evaporated
  4. customchromatographed (0-20% methanol/DCM)

Sources & evidence

ORD record
ord-04ed99d311384ae9987e0ff0040d1e14
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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