Water → HCID 68598110, compound

HRID 1943165Notes

Reaction equation

HRID 1943165 reaction equation
[CH2:1]1[C:9]2[CH:8]=[C:7]([C:10](OCC)=[O:11])[N:6]=[CH:5][C:4]=2[CH2:3][O:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:1]1[C:9]2[CH:8]=[C:7]([CH2:10][OH:11])[N:6]=[CH:5][C:4]=2[CH2:3][O:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68596203HCID 68596203, compound

Product 1

HCID 68598110HCID 68598110, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 1,3-dihydrofuro[3,4-c]pyridine-6-carboxylate (0.871 g, 4.51 mmol) in THF (20 ml) at −78° C. under argon was treated with LiAlH4 (1M in THF) (4.51 ml, 4.51 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 (66 mg, 10%).

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-146ce6543c8642e986ea81f3fc10e28c
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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