Sodium Hydroxide → HCID 67775438, compound

HRID 1808792Notes

Reaction equation

HRID 1808792 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C@@H:8]([CH:15]([CH3:17])[CH3:16])[C:9]([N:11]1[CH2:14][CH2:13][CH2:12]1)=O.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[N:11]1([CH2:9][C@@H:8]([NH2:7])[CH:15]([CH3:17])[CH3:16])[CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 52180852HCID 52180852, compound2×

Product 1

HCID 67775438HCID 67775438, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a 1M solution of LAH in THF (19.2 mL, 19.2 mmol) was (S)-2-amino-1-(azetidin-1-yl)-3-methylbutan-1-one (Compound T) (2 g, 12.8 mmol) in THF (12.8 mL) added (over approximately 30 min) at 0° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 1 h and heated at 60° C. for 6 h. The reaction was cooled to 0° C. Water (0.73 mL) was slowly added, followed by 15% aq. NaOH (0.73 mL) and additional water (2.2 mL). The reaction mixture was warmed to rt and stirred for 1 h. Celite and Na2SO4 were added. The mixture was filtered and the filtrate concentrated under reduced pressure to give the title compound (1.14 g, 63%). 1H NMR (400 MHz, CDCl3) δ 3.29-3.04, 2.51-2.39, 2.37-2.21, 2.14-1.96, 1.60-1.47, 1.34, 0.94-0.76. Total no of protons: 18.

Workup

  1. additionadded (over approximately 30 min) at 0° C. under a nitrogen atmosphere
  2. temperatureThe reaction was cooled to 0° C
  3. temperatureThe reaction mixture was warmed to rt
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-0c77a1cd52934ae4936f6ce7fda879f1
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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