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Triethylamine → HCID 70202469, compound

HRID 580565
Notes
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Reaction equation

HRID 580565 reaction equation
[NH2:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[C:22]([O:26][C:27](ON=C(C1C=CC=CC=1)C#N)=[O:28])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1>[NH3:1].[CH2:8]([N:4]1[CH2:5][C@@H:6]([CH3:7])[C@H:2]([NH:1][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 57429453(3s,4r)-1-Benzyl-4-methylpyrrolidin-3-amine

Product 2

HCID 222AmmoniaHCID 70202469HCID 70202469, compoundYield 171.7%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of trans-3-amino-1-benzyl-4-methylpyrrolidine hydrocarbonate (4.0 g) and triethylamine (3.2 g) in 50% aqueous dioxane (50 ml) was added t-butoxycarbonyloxyimino-2-phenylacetonitrile (Boc-ON, 5.8 g) with stirring at room temperature. After stirring for 3 hours, the reaction mixture was poured into ice-water and extracted with ether. The organic layer was washed 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica-gel column chromatography eluting with benzene to chloroform:methanol:concentrated aqueous ammonia (10:10:1) to give the title compound (5.24 g). Recrystallization from hexane gave colorless needles (5.04 g), mp 79°-80° C.

Workup

  1. stirringAfter stirring for 3 hours
  2. extractionextracted with ether
  3. washThe organic layer was washed 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica-gel column chromatography
  7. washeluting with benzene to chloroform

Sources & evidence

ORD record
ord-834b088371154c29b808075bae55668f
Source dataset
uspto-grants-1988_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04753953

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes