Water → 1,2,3,5,6,8a-Hexahydroindolizine-7-methanol

HRID 1274235Notes

Reaction equation

HRID 1274235 reaction equation
[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][C:7]([C:10](OCC)=[O:11])=[CH:8]2)[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]1[CH:9]2[N:4]([CH2:5][CH2:6][C:7]([CH2:10][OH:11])=[CH:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22120924Ethyl 1,2,3,5,6,8a-hexahydroindolizine-7-carboxylate

Product 1

HCID 221209331,2,3,5,6,8a-Hexahydroindolizine-7-methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1,2,3,5,6,8a-hexahydroindolizine-7-carboxylate (D1, 0.89 g, 4.6 mmol) was stirred under Ar in dry THF (50 ml) as lithium aluminium hydride (0.35 g, 9.2 mmol) was added portionwise. After 30 min, the reaction was worked up by successive addition of water (0.35 ml), 10% NaOH (0.35 ml) and water (1.05 ml). The solid was filtered off, and the filtrate was evaporated to yield the title compound (0.67 g, 97%) as a brown oil.

Workup

  1. additionwas added portionwise
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-84bee37117a24bd39308a70e372cb6f6
Source dataset
uspto-grants-2000_12
Patent number
US06156783

Reaction notes

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