Aluminium lithium hydride → (-)-Methamphetamine

HRID 2367265Notes

Reaction equation

HRID 2367265 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C[C:8]([N:11]([C@H:15]([CH3:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C(=O)[O-])(C)C>C1COCC1>[CH3:8][NH:11][C@H:15]([CH3:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86659176HCID 86659176, compound

Product 1

HCID 36604(-)-MethamphetamineYield 105.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension LiAlH4 (0.77 g, 20.4 mmol) in THF (120 mL) was added a solution of 1,1-dimethylethyl[(1R)-1-methyl-2-phenylethyl]carbamate (2.4 g, 10.2 mmol) in THF (30.0 ml) dropwise at 0° C., and then the reaction mixture was heated at reflux for 2 hours. The mixture was cooled to 0° C., and quenched by addition of ice (1.0 g), then 15% aqueous sodium hydroxide (1.0 mL) followed by water (0.5 mL). The lithium salts were collected by filtration and washed with Et2O (200 mL). The filtrate was dried (Na2SO4), filtered and concentrated. The resulting residue was distilled at reduced pressure to afford the title compound (1.6 g) as a light yellow oil. LC-MS (ES) m/z=150 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customquenched by addition of ice (1.0 g)
  4. filtrationThe lithium salts were collected by filtration
  5. washwashed with Et2O (200 mL)
  6. dry with materialThe filtrate was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. distillationThe resulting residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-cef34ec4568b49d39ec8e00873a8e6df
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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