Triethylamine → HCID 86674913, compound

HRID 241600Notes

Reaction equation

HRID 241600 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([CH2:14][OH:15])[CH2:12][CH:11]2[CH:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH:13]([CH2:14][O:15][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:12][CH:11]2[CH:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66981875HCID 66981875, compound

Product 1

HCID 86674913HCID 86674913, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of 3-Hydroxymethyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (2.52 grams, 11.83 mmol) in dry dichloromethane (10 mL) was added triethylamine (2.5 mL, 17.75 mmol) followed by methanesulfonyl chloride (1.0 mL, 13.01 mmol). The reaction mixture was gradually warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with dichloromethane. Organic layer was washed with saturated sodium bicarbonate solution followed brine, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure and the crude product was purified by flash column chromatography using 230-400 mesh silica gel to obtain title compound, 3.09 grams as gummy liquid. Yield: 90%.

Workup

  1. washOrganic layer was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-224134fc7929420c83a1ebee7bdf68e0
Source dataset
uspto-grants-2014_02
Patent number
US08653071B2

Reaction notes

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