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Sodium Hydroxide → 1-Benzyl-3-(1-tert-butoxycarbonylaminocyclobutyl)pyrrolidine

HRID 1457991
Notes
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Reaction equation

HRID 1457991 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([NH2:17])[CH2:16][CH2:15][CH2:14]2)[CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[C:27]([O:31][C:32](=O)[O:33]C(C)(C)C)([CH3:30])([CH3:29])[CH3:28]>O1CCCC1.O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:13]2([NH:17][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH2:16][CH2:15][CH2:14]2)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 21226445Aluminium lithium hydrideHCID 221005151-Benzyl-4-(1-aminocyclobutyl)-2-pyrrolidone

Product 1

HCID 221004971-Benzyl-3-(1-tert-butoxycarbonylaminocyclobutyl)pyrrolidineYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 1.50 g (6.14 mmol) portion of 1-benzyl-4-(1-aminocyclobutyl)-2-pyrrolidone (fr. 2) was dissolved in 200.0 ml of tetrahydrofuran to which, with cooling in an ice bath, was subsequently added 932 mg (24.56 mmol) of lithium aluminum hydride in small portions. After 12 hours of stirring with heating under reflux, the reaction solution was cooled in an ice bath and mixed with 932 μl of water in small portions, 932 μl of 15% sodium hydroxide aqueous solution and 932 μl of water in that order. After 30 minutes of stirring at room temperature, insoluble material was removed by filtration and the solvent was evaporated. To the thus obtained syrup were added 70.0 ml of acetonitrile and then 1.69 ml (7.37 mmol) of di-tert-butylcarbonate at room temperature, followed by overnight stirring. After evaporation of the solvent, the resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 150 ml, 5% methanol-chloroform) to yield 525 mg (26%) of the title compound.

Workup

  1. temperaturewith cooling in an ice bath
  2. temperaturewith heating
  3. temperatureunder reflux
  4. temperaturethe reaction solution was cooled in an ice bath
  5. stirringAfter 30 minutes of stirring at room temperature
  6. custominsoluble material was removed by filtration
  7. customthe solvent was evaporated
  8. additionTo the thus obtained syrup were added 70.0 ml of acetonitrile
  9. stirringstirring
  10. customAfter evaporation of the solvent
  11. customthe resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 150 ml, 5% methanol-chloroform)

Sources & evidence

ORD record
ord-445d913e6127454098cd470c102198a0
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05849757

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes