HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2193077
Notes
Print preview

Reaction equation

HRID 2193077 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8471
Triethylamine
Solvent
HCID 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-e9977eee9f664b5e947f465da466f1ba
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329694B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes