Water → HCID 18694259, compound

HRID 1870898Notes

Reaction equation

HRID 1870898 reaction equation
[C:1]([N:5]1[CH2:10][CH:9]=[C:8]([C:11](OC)=[O:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]([N:5]1[CH2:6][CH:7]=[C:8]([CH2:11][OH:12])[CH2:9][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18694256HCID 18694256, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18694259HCID 18694259, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl 1-tert-butyl-1,2,3,6-tetrahydropyridine-4-carboxylate (D57) (855 mg; 4.3 mmol) in dry tetrahydrofuran (10 ml) was added to a stirred suspension of lithium aluminium hydride (223 mg; 58 mmol) in dry tetrahydrofuran (20 ml) at 0° C. over 5 minutes. After stirring at 0° C. for 1 h, water (0.22 ml), 10% sodium hydroxide (0.33 ml) and water (0.55 ml) were added, and stirring continued for 30 minutes. The mixture was filtered through kieselguhr, and the filtrate evaporated under reduced pressure to give the title compound as an orange oil (610 mg, 83%).

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. filtrationThe mixture was filtered through kieselguhr
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-f6364729947741b99e7b793af19a6248
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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