Methyl iodide → HCID 69707075, compound

HRID 981097Notes

Reaction equation

HRID 981097 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:27]I>O1CCCC1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([O:13][CH3:27])[C@H:10]([NH:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69706831trans-1-Benzyl-3-benzylmethylamino-4-hydroxypyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 69707075HCID 69707075, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

17.3 g (58 mmol) of crude trans-1-benzyl-3-benzylmethylamino-4-hydroxy-pyrrolidine in 80 ml of absolute tetrahydrofuran are added dropwise to 2.8 g (93.3 mmol) of 80% strength sodium hydride in 40 ml of absolute tetrahydrofuran and the mixture is heated under reflux at the same time. When the evolution of hydrogen has ended, 8.7 g (61 mmol) of methyl iodide are added dropwise and the mixture is then heated under reflux overnight. It is poured into ice-water and extracted with toluene, the extracts are dried with K2CO3, and concentrated and the residue is distilled.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux at the same time
  3. temperaturethe mixture is then heated
  4. temperatureunder reflux overnight
  5. extractionextracted with toluene
  6. dry with materialthe extracts are dried with K2CO3
  7. concentrationconcentrated
  8. distillationthe residue is distilled

Sources & evidence

ORD record
ord-0aaf4874fd2546268378becee940bc4a
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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