Water → HCID 57470870, compound

HRID 2066282Notes

Reaction equation

HRID 2066282 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 aluminum hydride (300 mg) was suspended in tetrahydrofuran (10 ml) under a nitrogen atmosphere at room temperature, and a solution of 3-(azetidin-1-ylcarbonyl)-1-benzhydrylazetidine (1.14 g) in tetrahydrofuran (30 ml) was added dropwise. After the dropwise addition, the reaction mixture was stirred at 60° C. for 2 hr. The reaction mixture was cooled in an ice water bath, and 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 provide the titled compound as a pale brown oil (1.115 g, quantitative).

Workup

  1. additionAfter the dropwise addition
  2. temperatureThe 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-b5126e0e58a74a409c71a5f02c185143
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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