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

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

Reactant 4

HCID 962Water2×

HCID 14798Sodium Hydroxide

HCID 21226445Aluminium lithium hydride

HCID 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

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.