Water → HCID 57470870, compound

HRID 1712654Notes

Reaction equation

HRID 1712654 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:11]([CH:13]2[CH2:16][N:15]([CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:14]2)=O)[CH2:10][CH2:9][CH2:8]1.O.[OH-].[Na+]>O1CCCC1>[N:7]1([CH2:11][CH:13]2[CH2:14][N:15]([CH:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:16]2)[CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57470869HCID 57470869, compound

Product 1

HCID 57470870HCID 57470870, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Lithium aluminium hydride (300 mg) was suspended in tetrahydrofuran (10 ml) at room temperature under a nitrogen atmosphere, and a solution of 3-(azetidin-1-ylcarbonyl)-1-benzhydrylazetidine (1.14 g) in tetrahydrofuran (30 ml) was added dropwise. After the addition, the reaction mixture was stirred at 60° C. for 2 hours. After the reaction mixture was cooled in an ice water bath, water (0.3 ml), a 5N aqueous solution of sodium hydroxide (0.3 ml) and water (0.9 ml) were added, followed by stirring overnight. Insoluble matter was removed by filtration, and washed with ethyl acetate (100 ml). The filtrate was concentrated under reduced pressure to give the title compound (1.115 g, quant.) as a pale brown oil.

Workup

  1. additionAfter the addition
  2. temperatureAfter the reaction mixture was cooled in an ice water bath
  3. stirringby stirring overnight
  4. customInsoluble matter was removed by filtration
  5. washwashed with ethyl acetate (100 ml)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-420db30ff9154884b98e457e17542322
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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