Iodoethane → HCID 67820205, compound

HRID 2253691Notes

Reaction equation

HRID 2253691 reaction equation
C(OC([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C@H:9]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:13][C:12](=[O:21])[CH2:11][CH2:10]1)=O)(C)(C)C.[CH3:31][C:32](C)([O-])C.[K+].C(I)C>C1COCC1>[CH2:31]([N:13]1[C@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:9]([NH:8][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])[CH2:10][CH2:11][C:12]1=[O:21])[CH3:32]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 23665647Potassium tert-butoxide2×HCID 67820261HCID 67820261, compound

Product 1

HCID 67820205HCID 67820205, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere in a round-bottom flask were placed 50 mg (0.12 mmol) of cis-5-(N-tert-butoxycarbonyl-2-methoxybenzylamino)-2-oxo-6-phenylpiperidine and 0.2 mL of THF. To the system were added 13.5 mg (0.12 mmol) of potassium tert-butoxide and 20 μL (0.24 mmol) of ethyl iodide. The reaction mixture was stirred at room temperature for 3 hours (during this period, additional potassium tert-butoxide (13.5 mg) and ethyl iodide (20 μL) were added to the system). The mixture was partitioned between methylene chloride and aqueous sodium bicarbonate, the layers were separated and the aqueous phase was extracted with three portions of methylene chloride. The combined organic fractions were dried (sodium sulfate) and concentrated with a rotary evaporator. The crude material was purified by flash column chromatography using 3:97 methanol/chloroform as the eluant to obtain 42 mg of cis-N-ethyl-5-(2-methoxybenzylamino)-2-oxo-6-phenylpiperidine.

Workup

  1. customUnder a nitrogen atmosphere in a round-bottom flask were placed
  2. customThe mixture was partitioned between methylene chloride and aqueous sodium bicarbonate
  3. customthe layers were separated
  4. extractionthe aqueous phase was extracted with three portions of methylene chloride
  5. dry with materialThe combined organic fractions were dried (sodium sulfate)
  6. concentrationconcentrated with a rotary evaporator
  7. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-f5cfa5cc98334de49182bfdda1a22c65
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

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