Tetrahydrofuran → Tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

HRID 39705Notes

Reaction equation

HRID 39705 reaction equation
O1CCCC1.[C:6]([C:8]1([CH2:21][CH2:22][OH:23])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)#[N:7].[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C(N(CC)CC)C>[C:6]([C:8]1([CH2:21][CH2:22][O:23][S:25]([CH3:24])(=[O:27])=[O:26])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:10][CH2:9]1)#[N:7]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 60064207Tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylate

Product 1

HCID 86617989Tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 10 mL of a tetrahydrofuran solution containing 1.0 g of tert-butyl 4-cyano-4-(2-hydroxyethyl)piperidine-1-carboxylate, 0.77 mL of triethylamine was added at room temperature, thereto was added 0.37 mL of methane sulfonyl chloride under cooling with ice, and the mixture was stirred at the same temperature for 2 hours and 30 minutes. The reaction mixture was added with an aqueous saturated sodium hydrogen carbonate solution and ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.3 g of a brown oily substance, tert-butyl 4-cyano-4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate.

Workup

  1. additionwas added at room temperature
  2. temperatureunder cooling with ice
  3. customThe organic layer was separated
  4. washwashed 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-9801021c71b64ca89316160c934c3309
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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