Triethylamine → N-(2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl)methanesulfonamide

HRID 2223872Notes

Reaction equation

HRID 2223872 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][NH2:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(=O)(O)[O-].[Na+]>ClCCl>[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][NH:29][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 597149732-[1-[2-(Tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethylamine

Product 1

HCID 59714854N-(2-[1-[2-(tert-Butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethylamine (409 mg) dissolved in dichloromethane (10 mL) was added triethylamine (0.28 mL). Methanesulfonyl chloride (0.12 mL) was added to the solution under ice cooling, and it was stirred at that temperature for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the solution, and it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then, the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=6:1) to give the title compound (327 mg).

Workup

  1. extractionwas extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-5540631c71a74132934b5e529974d45e
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…