Triethylamine → HCID 53628938, compound

HRID 1784664Notes

Reaction equation

HRID 1784664 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].CS(Cl)(=O)=O.OCC1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]2)=[CH:17][CH:16]=1.N1CCCC1>ClCCl>[N:3]1([CH2:6][C:7]2[CH:20]=[CH:19][C:18]([CH:21]3[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]3)=[CH:17][CH:16]=2)[CH2:4][CH2:5][CH2:2][CH2:1]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 67117411HCID 67117411, compound

Product 1

HCID 53628938HCID 53628938, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.47 g, 3.4 mmol) and methanesulfonyl chloride (0.12 ml, 1.6 mmol) were added to an ice-cooled solution of 3-(4-hydroxymethylphenyl)-1-(tert-butoxycarbonyl)piperidine (0.39 g, 1.34 mmol) in dichloromethane and stirred for 7.5 hr. Pyrrolidine (1.0 ml, 12 mmol) was added to the solution and stirred overnight. Organic solvents were removed under reduced pressure after addition of water and extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. Removal of the solvent under reduced pressure and the residue was purified by silica gel chromatography (eluent; ethyl acetate to ethyl acetate/methanol=1/1, then methanol only) to give 3-(4-(1-pyrrolidinyl)methylphenyl)-1-(tert-butoxycarbonyl)piperidine (0.26 g, 56%).

Workup

  1. stirringstirred overnight
  2. customOrganic solvents were removed under reduced pressure
  3. additionafter addition of water
  4. extractionextracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-006a6d8fe70a42688554cce043580d69
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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