HCID 7019137, compound → HCID 57948127, compound

HRID 340949Notes

Reaction equation

HRID 340949 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-3148d334421f4080a4d00043c1194526
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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