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

HRID 77422Notes

Reaction equation

HRID 77422 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-].O.[OH-].[Na+]>C1COCC1>[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

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66664280((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-ylmethanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ((S)-6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)pyrrolidin-1-ylmethanone (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 precipitate which formed 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+).

Workup

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

Sources & evidence

ORD record
ord-2faf78021fcb43a29a493b11506cb2c7
Source dataset
uspto-grants-2014_09
Patent number
US08841290B2

Reaction notes

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