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Water → 3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]-1-[1-(S)-phenylethyl]Pyrrolidine

HRID 600899
Notes
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Reaction equation

HRID 600899 reaction equation
[C:1]([O:5][C:6]([N:8]([C:10]1([C@H:13]2[CH2:17][CH2:16][N:15]([C@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])[C:14]2=O)[CH2:12][CH2:11]1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:10]1([C@@H:13]2[CH2:17][CH2:16][N:15]([C@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])[CH2:14]2)[CH2:11][CH2:12]1)[CH3:9])=[O:7])([CH3:2])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 672717743-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)amino]cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidin-2-one

Product 1

HCID 672710823-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)Amino]Cyclopropyl]-1-[1-(S)-phenylethyl]PyrrolidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

3-(R)-[1-[N-(tert-butoxycarbonyl)-N-(methyl)amino]cyclopropyl]-1-[1-(S)-phenylethyl]pyrrolidin-2-one (7.53 g, 21.0 mmol) was dissolved in anhydrous tetrahydrofuran (70 ml) and a 1.0M borane-tetrahydrofuran complex/tetrahydrofuran solution (63.0 ml, 63.0 mmol) was added dropwise gradually thereto while stirring and cooling with ice. After completion of dripping, it was stirred at room temperature for 20 hours. After slowly adding an aqueous solution (72 ml) of potassium carbonate (7.22 g) while cooling with ice, it was heated under reflux for 1.5 hours. After letting the reaction solution cool to room temperature, water (150 ml) was added, extraction with ethyl acetate (200 ml×2) was performed, and then the combined organic layer was washed with saturated saline solution (200 ml) and then dried over anhydrous sodium sulfate. After filtering, the filtrate was concentrated under a reduced pressure, the concentrate was applied to a silica gel chromatography, and 7.19 g (99%) of the title compound was obtained in the form of a colorless syrup from a chloroform:methanol=50:1 eluate.

Workup

  1. temperaturecooling with ice
  2. stirringit was stirred at room temperature for 20 hours
  3. temperaturewhile cooling with ice, it
  4. temperaturewas heated
  5. temperatureunder reflux for 1.5 hours
  6. extractionextraction with ethyl acetate (200 ml×2)
  7. washthe combined organic layer was washed with saturated saline solution (200 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtering
  10. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-e9346203cd9249d08fb3997c4197f19c
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902226B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes