Aluminium lithium hydride → HCID 178484887, compound

HRID 340947Notes

Reaction equation

HRID 340947 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1)[C:10](O)=[O:11])=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:17]1[CH:18]=[C:14]([CH2:13][C@H:9]([NH:8][CH3:6])[CH2:10][OH:11])[N:15]=[CH:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178454169HCID 178454169, compound

Product 1

HCID 178484887HCID 178484887, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-(1H-imidazol-4-yl)propanoic acid (1.0 g, 3.92 mmol) in THF (20 mL) was added LAH (2 M, 10 mL, 20 mmol) at 0-5° C. The reaction mixture was stirred at 0-5° C. for 30 min and heat to reflux for 2 h. The reaction mixture was cooled to 0-5° C. and quenched with water (0.8 mL), NaOH (0.8 mL), and water (2.4 mL). The resulting suspension was stirred RT for 30 min and filtered. The filtrate was concentrated to give (S)-3-(1H-imidazol-4-yl)-2-(methylamino)propan-1-ol (400 mg, crude), which was used without further purification. LRMS (M-Boc+H+) m/z 156.1.

Workup

  1. temperatureheat
  2. temperatureto reflux for 2 h
  3. temperatureThe reaction mixture was cooled to 0-5° C.
  4. customquenched with water (0.8 mL), NaOH (0.8 mL), and water (2.4 mL)
  5. stirringThe resulting suspension was stirred RT for 30 min
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-aa74cfc3cd0642508051ab15d75f2738
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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