Diethyl Ether → (1S)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamine

HRID 606293Notes

Reaction equation

HRID 606293 reaction equation
C(O[C:4](=O)[NH:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC>C1COCC1>[CH3:4][NH:5][C@@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4569760Ethyl 1,2,3,4-tetrahydronaphthalen-1-ylcarbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 7128547(1S)-1,2,3,4-Tetrahydro-N-methyl-1-naphthalenamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

(1,2,3,4-Tetrahydro-naphthalen-1-yl)-carbamic acid ethyl ester (5.0 g, 22.8 mmol) is added slowly under nitrogen to a suspension of LiAlH4 (2.6 g, 68 mmol) in THF (50 mL). The resulting mixture is heated at 75° C. with stirring for 2 hours. On cooling, Na2SO4.10H2O (15.0 g) and ether (100 mL) are added to the mixture. The resulting mixture is stirred at room temperature for 1 hour, filtered through celite, and concentrated in vacuo. 1 N HCl (20 mL) and ether (20 ML) are added to the residue. The organic layer is separated and discarded. The aqueous layer is basified with 1 N NaOH and extracted with CH2Cl2 (2×25 mL). The combined extract is washed with water (2×), dried (Na2SO4) and concentrated to give (S)-methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine as an oil. [α]RT=−10.6 (0.02, EtOH). 1H NMR (CDCl3) 7.30 (m, 1H), 7.06-7.20 (m, 3H), 3.66 (t, 1H), 2.78 (m, 2H), 2.50 (s, 3H), 1.70-2.00 (m, 4H).

Workup

  1. temperatureOn cooling
  2. stirringThe resulting mixture is stirred at room temperature for 1 hour
  3. filtrationfiltered through celite
  4. concentrationconcentrated in vacuo
  5. addition1 N HCl (20 mL) and ether (20 ML) are added to the residue
  6. customThe organic layer is separated
  7. extractionextracted with CH2Cl2 (2×25 mL)
  8. extractionThe combined extract
  9. washis washed with water (2×)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9d5507b4fc2e48c2924b7ff380203eb0
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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