Tetrahydrofuran → 1-Tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate

HRID 39669Notes

Reaction equation

HRID 39669 reaction equation
O1CCCC1.[OH:6][CH2:7][CH2:8][CH2:9][C:10]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>O.C(OCC)(=O)C>[CH3:35][S:36]([O:6][CH2:7][CH2:8][CH2:9][C:10]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)(=[O:38])=[O:37]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578152391-Tert-butyl 4-ethyl 4-(3-hydroxypropyl)piperidine-1,4-dicarboxylate

Product 1

HCID 578155261-Tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 20 mL of a tetrahydrofuran solution containing 1.7 g of 1-tert-butyl 4-ethyl 4-(3-hydroxypropyl)piperidine-1,4-dicarboxylate, 0.82 mL of triethylamine and 0.58 mL of methane sulfonylchloride were added at 5° C., and the mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.9 g of a colorless oily substance, 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate.

Workup

  1. additionwere added at 5° C.
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-93e876b0154a43d2a9ecd0e7b7dab8bb
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…