Pyridine → HCID 54158307, compound

HRID 1752416Notes

Reaction equation

HRID 1752416 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][NH2:8])[CH2:4][O:3]1.N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(OCC)C>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][NH:8][S:17]([CH3:16])(=[O:19])=[O:18])[CH2:4][O:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-

Product 1

HCID 54158307HCID 54158307, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of the (2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (4.616 g, 35.19 mmol) in diethylether (100 mL) was added pyridine (2.90 mL, 35.9 mmol). A solution of methanesulfonyl chloride (2.75 mL, 35.4 mmol) in diethylether (50 mL) was added to the amine solution over 30 minutes. After stirring for 2 h, the reaction was washed once with 25 mL water then twice with 25 mL brine. The organic layer was separated, dried over MgSO4, filtered, and evaporated to a residue. The residue was chromatographed over silica gel with 0-100% EtOAc in hexanes. The product fractions were evaporated in vacuo to give N-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)methanesulfonamide as a near-colorless oil (0.875 g, 4.18 mmol, 12% yield). 1H NMR (400 MHz, DMSO-d6): 7.17 (1H, t, J=6.4 Hz), 4.13-4.06 (1H, m), 3.98 (1H, dd, J=8.3 Hz, 6.4 Hz), 3.66 (1H, dd, J=8.3 Hz, 5.7 Hz), 3.09-2.98 (2H, m), 2.91 (3H, s), 1.33 (3H, s), 1.26 (3H, s).

Workup

  1. washthe reaction was washed once with 25 mL water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated to a residue
  6. customThe residue was chromatographed over silica gel with 0-100% EtOAc in hexanes
  7. customThe product fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-f5685c898d5342a3b8e4c994872b3b7c
Source dataset
uspto-grants-2015_10
Patent number
US09163008B2

Reaction notes

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