Water → HCID 67773219, compound

HRID 1808782Notes

Reaction equation

HRID 1808782 reaction equation
[N:1]1([C:5](=O)[C@@H:6]([NH:10][C:11](=O)OC(C)(C)C)[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[N:1]1([CH2:5][C@@H:6]([NH:10][CH3:11])[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 52180842tert-Butyl [(2S)-1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-yl]carbamate2×

Product 1

HCID 67773219HCID 67773219, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

A solution of (S)-tert-butyl 1-(azetidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (Compound D) (20 g, 78 mmol) in THF (200 mL) was dropwise charged (over approximately 90 min) to a jacketed reactor containing a 1M solution of LAH in THF (200 mL, 200 mmol) under a nitrogen atmosphere. The resultant mixture was heated at 60° C. over night. The reaction was cooled to −5° C. and H2O (7.6 mL) was slowly added. The mixture was diluted with THF (200 mL). A 15% aq. NaOH (7.6 mL) solution and additional H2O (22.8 mL) were added. The mixture was warmed to 25° C. and stirred for 1 h. The slurry was filtered and solids were washed with THF. The filtrate was concentrated under reduced pressure to give the title compound (1.7 g, 79%). The obtained crude product was used without further purification. 1H NMR (400 MHz, CH3OD) δ 0.86, 1.75-1.90, 1.94-2.18, 2.18-2.36, 2.38, 2.99-3.29. Total no of protons: 19.

Workup

  1. temperatureThe mixture was warmed to 25° C.
  2. filtrationThe slurry was filtered
  3. washsolids were washed with THF
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-196417209bcd48eeb8875e597abf4f7e
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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