Aluminium lithium hydride → HCID 86682893, compound

HRID 1522857Notes

Reaction equation

HRID 1522857 reaction equation
C([O:4][CH2:5][C@@H:6]([N:8]1[C:12](=O)[CH2:11][C:10]([CH3:15])([CH3:14])[C:9]1=O)[CH3:7])(=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH3:14][C:10]1([CH3:15])[CH2:11][CH2:12][N:8]([C@@H:6]([CH3:7])[CH2:5][OH:4])[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86682892HCID 86682892, compound

Product 1

HCID 86682893HCID 86682893, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (S)-2-(3,3-dimethyl-2,5-dioxopyrrolidin-1-yl)propyl acetate (6.15 g, 27.1 mmol) in anhydrous diethyl ether (20 mL) was added to a suspension of LiAlH4 (3.0 g, 79 mmol) in anhydrous diethyl ether (250 mL) at room temperature under nitrogen atmosphere. After stirring at room temperature overnight, the reaction mixture was quenched with H2O (3 mL). The resulting suspension was filtered, and the filter cake was washed with ethyl acetate (50 mL). The combined filtrate was concentrated under reduced pressure, and the residue was purified on a silica gel column (eluting with DCM/MeOH=20/1) to give (S)-2-(3,3-dimethylpyrrolidin-1-yl)propan-1-ol (2.37 g, 59%). 1H NMR (CDCl3): δ 3.53 (dd, 1H), 3.27 (dd, 1H), 2.70 (m, 3H), 2.37 (s, 2H), 1.55 (m, 2H), 1.07 (s, 3H), 1.06 (s, 3H), 0.94 (d, 3H); LCMS: 158 (M+H)+.

Workup

  1. customthe reaction mixture was quenched with H2O (3 mL)
  2. filtrationThe resulting suspension was filtered
  3. washthe filter cake was washed with ethyl acetate (50 mL)
  4. concentrationThe combined filtrate was concentrated under reduced pressure
  5. customthe residue was purified on a silica gel column (eluting with DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-920202bc00534e02929422a5e9e86744
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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