Aluminium lithium hydride → HCID 45099445, compound

HRID 861368Notes

Reaction equation

HRID 861368 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:14][N:8]2[CH2:9][CH2:10][NH:11][C:12](=O)[C@@H:7]2[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:2][CH2:3][C@@H:5]1[CH2:14][N:8]2[CH2:9][CH2:10][NH:11][CH2:12][C@@H:7]2[CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70198608(7S,8aS)-7-methoxycarbonyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one

Product 1

HCID 45099445HCID 45099445, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.75 g (8.84 mmol) of (7S,8aS)-7-methoxycarbonyl-1,2,3,4,6,7,8,8 a-octahydro-pyrrolo[1,2-a]pyrazin-1-one (Preparation 11) in 100 mL of THF was added dropwise to a suspension of 0.67 g (18 mmol) of lithium aluminum hydride in 100 mL of refluxing THF. After stirring for 1 h, the solution was cooled and carefully quenched with 0.67 mL of water, 0.67 mL of 15% sodium hydroxide, and 2.0 mL of water. The precipitate was filtered and the filtrate was concentrated to give 1.4 g of (7S,8aS)-7-hydroxymethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine of sufficient purity for use in subsequent reactions.

Workup

  1. temperaturethe solution was cooled
  2. customcarefully quenched with 0.67 mL of water, 0.67 mL of 15% sodium hydroxide, and 2.0 mL of water
  3. filtrationThe precipitate was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-69d1975c2d794874ac25a2591ea62638
Source dataset
uspto-grants-1998_02
Patent number
US05714487

Reaction notes

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