Sodium Hydroxide → (S)-6-Pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine

HRID 1913805Notes

Reaction equation

HRID 1913805 reaction equation
[NH2:1][C@H:2]1[CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:12]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=O)[CH:6]=[CH:5][C:4]=2[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].COC1CCN(CC2C=C3C(=CC=2)C[C@@H](N)CC3)CC1.N1(CC2C=C3C(=CC=2)C[C@@H](N)CC3)CCCCCC1>C1COCC1.O>[N:14]1([CH2:12][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH2:3][C@@H:2]([NH2:1])[CH2:11][CH2:10]3)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66663494HCID 66663494, compoundHCID 66664280((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-ylmethanoneHCID 67545539(S)-6-(4-methoxypiperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-ylamine

Product 1

HCID 66663464(S)-6-Pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-yl-methanone (0.49 g) in THF (5 ml) was added dropwise to a suspension of lithium aluminum hydride (0.60 g) in THF (10 ml). The mixture was stirred at RT for one hour. Water (0.6 ml) was cautiously added dropwise, followed by sodium hydroxide solution (16%; 2 ml) and water again (2 ml). The resulting precipitate was filtered off and the filtrate was concentrated. The residue was taken up in hydrochloric acid (1N) and the solution was washed with diethyl ether. The aqueous phase was basified with concentrated sodium hydroxide solution and extracted three times with dichloromethane (DCM). The combined organic phases were dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 230.36 (C15H22N2); MS (ESI): 231 (M+H+). In an analogous manner, (S)-6-(4-methoxypiperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-2-ylamine and (S)-6-azepan-1-ylmethyl-1,2,3,4-tetrahydronaphthalen-2-ylamine were prepared.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. washthe solution was washed with diethyl ether
  4. extractionextracted three times with dichloromethane (DCM)
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe product was thus obtained with the molecular weight of 230.36 (C15H22N2)

Sources & evidence

ORD record
ord-c0fa8c0deff34b8295a07eb279b0f3ca
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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