HCID 7019137, compound → HCID 57948127, compound

HRID 409811Notes

Reaction equation

HRID 409811 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:10]([O-])=[O:11])=O)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:6][NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 7019137HCID 7019137, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57948127HCID 57948127, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-(pyridin-2-yl)propanoate (1.05 g, 3.96 mmol) in THF (20 mL) was added LAH (2 M in THF, 4.0 mL, 8.0 mmol) at 0° C. The resulting solution was stirred at 0° C. for 30 min and heated to reflux for 2 h. The reaction mixture was cooled and quenched with water (0.32 mL), NaOH (3 N, 0.32 mL), and water (0.96 mL). The resulting suspension was stirred at RT for 30 min. The mixture was filtered and the filtrate was concentrate to give (S)-2-(methylamino)-3-(pyridin-2-yl)propan-1-ol (510 mg, crude), which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThe reaction mixture was cooled
  4. customquenched with water (0.32 mL), NaOH (3 N, 0.32 mL), and water (0.96 mL)
  5. stirringThe resulting suspension was stirred at RT for 30 min
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrate

Sources & evidence

ORD record
ord-dc4ccabccede42d18902fd77c840f83f
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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