Piperidine → HCID 59519082, compound

HRID 1161846Notes

Reaction equation

HRID 1161846 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12]OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH2:12][N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Product 1

HCID 59519082HCID 59519082, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 3-methanesulfonyloxymethylazetidine-1-carboxylic acid tert-butyl ester (0.36 g, 1.40 mmol) in toluene (2 mL) was added piperidine (0.7 mL, 7.00 mmol) and the resultant mixture was heated to 110° C. in a sealed tube for 18 h. The solution was concentrated in vacuo, the crude residue dissolved in DCM and washed with 0.5 N KOH (aq.) (1×) and brine (1×). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The resultant oil was purified by chromatography on silica gel with MeOH:DCM (1:19, v/v) as eluent to afford 3-piperidin-1-ylmethylazetidine-1-carboxylic acid tert-butyl ester (180 mg, 0.70 mmol, 50%) as an oil.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe crude residue dissolved in DCM
  3. washwashed with 0.5 N KOH (aq.) (1×) and brine (1×)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant oil was purified by chromatography on silica gel with MeOH:DCM (1:19, v/v) as eluent

Sources & evidence

ORD record
ord-be087d18b92643de97ca2123af9b6575
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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