Water → HCID 23153585, compound

HRID 492940Notes

Reaction equation

HRID 492940 reaction equation
C(O[C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH:15]2[CH2:18][N:17]([C:19](OC(C)(C)C)=O)[CH2:16]2)[CH2:11][CH2:10]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:6][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH:15]2[CH2:16][N:17]([CH3:19])[CH2:18]2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23153085HCID 23153085, compound

Product 1

HCID 23153585HCID 23153585, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-[4-(tert-butoxycarbonylamino)piperidin-1-yl]azetidine-1-carboxylate (2.49 g) in tetrahydrofuran (100 ml) was added lithium aluminium hydride (930 mg) while stirring in an ice bath, followed by stirring under a nitrogen atmosphere in an ice bath for 10 min and at room temperature for 10 min. The reaction mixture was refluxed under a nitrogen atmosphere for 1.5 hrs. The reaction mixture was cooled in an ice bath, and then water (0.93 ml), a 5N aqueous solution of sodium hydroxide (0.93 ml), and water (4.65 ml) were added thereto in this order, followed by stirring at room temperature for 24 hrs. The insoluble portion was filtered off and washed with ethyl acetate to give a filtrate, which was concentrated to provide the titled compound (1.07 g, 83.4%) as a pale yellow oil.

Workup

  1. stirringby stirring under a nitrogen atmosphere in an ice bath for 10 min and at room temperature for 10 min
  2. temperatureThe reaction mixture was refluxed under a nitrogen atmosphere for 1.5 hrs
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. stirringby stirring at room temperature for 24 hrs
  5. filtrationThe insoluble portion was filtered off
  6. washwashed with ethyl acetate
  7. customto give a filtrate, which
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-ad6eb1c31d5544f99b05e088a9d1060f
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

Loading…