Water → 1-(5-Methylthiophen-2-yl)ethan-1-amine

HRID 911350Notes

Reaction equation

HRID 911350 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[CH3:11])=[N+]=[N-].CCOC(C)=O.O>C1COCC1>[NH2:7][CH:10]([C:12]1[S:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 576559232-(1-Azidoethyl)-5-methylthiophene

Product 1

HCID 42794271-(5-Methylthiophen-2-yl)ethan-1-amineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium aluminum hydride (29 mg, 0.72 mmol) to a solution of (±)-2-(1-azidoethyl)-5-methylthiophene (100 mg, 0.59 mmol) in anhydrous THF (5 mL). Stir at room temperature overnight. Work-up the mixture with EtOAc and water. Filter the mixture over Celite®. Separate and wash the organic phase with brine. Dry over Na2SO4, filter and concentrate in vacuo. Purify by SCX chromatography. Rinse with DCM/methanol (1:1), load the crude mixture in methanol and elute sequentially with methanol and 1N ammonia in methanol to obtain the title compound as an oil (80 mg, 95%). GC-MS m/z 141 (M+).

Workup

  1. filtrationFilter the mixture over Celite®
  2. customSeparate
  3. washwash the organic phase with brine
  4. dry with materialDry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by SCX chromatography
  8. washRinse with DCM/methanol (1:1), load the crude mixture in methanol
  9. washelute sequentially with methanol and 1N ammonia in methanol

Sources & evidence

ORD record
ord-b67c75e613614809b2a4b0e4721c3530
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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