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

HRID 1457990
Notes
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Reaction equation

HRID 1457990 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 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A 1.01 g (4.13 mmol) portion of 1-benzyl-4-(1-aminocyclobutyl)-2-pyrrolidone (fr. 1) was dissolved in 150.0 ml of tetrahydrofuran. Thereto was subsequently added 627 mg (16.52 mmol) of lithium aluminum hydride in small portions under ice cooling. After 12 hours of stirring with heating under reflux, the reaction solution was cooled in an ice bath and mixed with 627 μl of water in small portions, 627 μl of 15% sodium hydroxide aqueous solution and 627 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 50.0 ml of acetonitrile and then 1.14 ml (4.96 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 100 ml, 5% methanol-chloroform) to yield 212 mg (16%) of the title compound.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperaturethe reaction solution was cooled in an ice bath
  4. stirringAfter 30 minutes of stirring at room temperature
  5. custominsoluble material was removed by filtration
  6. customthe solvent was evaporated
  7. additionTo the thus obtained syrup were added 50.0 ml of acetonitrile
  8. stirringstirring
  9. customAfter evaporation of the solvent
  10. customthe resulting residue was purified by a silica gel column chromatography (230-400 mesh silica gel 100 ml, 5% methanol-chloroform)

Sources & evidence

ORD record
ord-5099cc1c65fb4cfdb831c4dfdf29ad0d
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