Aluminium lithium hydride → (R)-N-methyl-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine

HRID 1444714Notes

Reaction equation

HRID 1444714 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C@H:14]([NH:18][C:19](=O)OC(C)(C)C)[CH2:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1>[CH3:19][NH:18][C@H:14]1[C:15]2[C:10](=[CH:9][C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:17][CH:16]=2)[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 56594897(R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Product 1

HCID 68679772(R)-N-methyl-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 50 mL of dry toluene, 2.0 g (5.8 mmol) of (R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate and 1.5 g (41 mmol) of lithium aluminum hydride were combined and gently refluxed for 24 h. Next the mix was quenched with 5 g of sodium sulfate decahydrate and allowed to stir for 2 h. The mix was then filtered over celite and the pad was washed with ethyl acetate several times. The filtrate was then concentrated and the crude was purified on silica using 0 to 5% MeOH (10% ammonium hydroxide) in ethyl acetate to give the product. MS 259 (ESI, pos. ion).

Workup

  1. temperaturegently refluxed for 24 h
  2. customNext the mix was quenched with 5 g of sodium sulfate decahydrate
  3. filtrationThe mix was then filtered over celite
  4. washthe pad was washed with ethyl acetate several times
  5. concentrationThe filtrate was then concentrated
  6. customthe crude was purified on silica using 0 to 5% MeOH (10% ammonium hydroxide) in ethyl acetate
  7. customto give the product

Sources & evidence

ORD record
ord-4b672c3a030b4ecbb290c49910330133
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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