Ethyl Acetate → HCID 23367041, compound

HRID 2102434Notes

Reaction equation

HRID 2102434 reaction equation
[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH:3]([C:11](OCC)=[O:12])[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1.O>[CH2:1]1[CH:10]2[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH:3]([CH2:11][OH:12])[CH2:2]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12519345Ethyl octahydro-2H-quinolizine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23367041HCID 23367041, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl octahydro-2H-quinolizine-3-carboxylate (2.35 g, 11.1 mmol) was added dropwise to a stirred suspension of lithium aluminum hydride (1 M solution in tetrahydrofuran, 33 mL, 33 mmol) in tetrahydrofuran (50 mL) at 0° C. The reaction was stirred at room temperature for 3 h. The mixture was cooled in an ice bath and ethyl acetate (6 mL) was added slowly, followed by water (1.25 mL), 15% aqueous sodium hydroxide solution (5 mL) and water (1.25 mL). The mixture was filtered through a pad of celite and washed with ether. The filtrate was concentrated in vacuo and dried rigorously to afford octahydro-2H-quinolizin-3-ylmethanol as a yellow oil (1.66 g, 9.82 mmol, 88% yield). MS (EI) for C10H19NO: 170 (MH+).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationThe mixture was filtered through a pad of celite
  3. washwashed with ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customdried rigorously

Sources & evidence

ORD record
ord-21ea25bb82d9409baac728e61b0b100d
Source dataset
uspto-grants-2009_08
Patent number
US07576074B2

Reaction notes

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