Triethylamine → 2-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonate

HRID 1437220Notes

Reaction equation

HRID 1437220 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:16][CH2:15][CH2:14][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 230901662-(N-tert-Butoxycarbonylpiperidin-2-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester (229 mg) obtained from Referential Example 77 and triethylamine (209 μL) were dissolved in methylene chloride (5 mL) To the resultant solution, methanesulfonyl chloride (116 μL) was added at room temperature, followed by stirring for 30 minutes. The residue obtained by removal through evaporation of the reaction solvent under reduced pressure was partitioned between water and methylene chloride. The organic layer was sequentially washed with water and saturated brine, and then dried over sodium sulfate anhydrate, followed by filtration. The solvent was evaporated under reduced pressure, to thereby give the title compound in the form of crystals (288 mg, 93%).

Workup

  1. additionwas added at room temperature
  2. customThe residue obtained by removal through evaporation of the reaction solvent under reduced pressure
  3. customwas partitioned between water and methylene chloride
  4. washThe organic layer was sequentially washed with water and saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cb72dbc54cee452db7a6cc4c5b704a6e
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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