Triethylamine → [3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo[3.3.1.03,7]non-1-yl]methyl methane sulfonate

HRID 1015509Notes

Reaction equation

HRID 1015509 reaction equation
[CH3:1][C:2]1([C:7]23[CH2:14][CH:13]4[CH2:15][C:9]([CH2:16][OH:17])([CH2:10][CH:11]2[CH2:12]4)[CH2:8]3)[O:6][CH2:5][CH2:4][O:3]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C1COCC1.CN(C1C=CN=CC=1)C.O>[CH3:25][S:26]([O:17][CH2:16][C:9]12[CH2:15][CH:13]3[CH2:12][CH:11]([CH2:10]1)[C:7]([C:2]1([CH3:1])[O:3][CH2:4][CH2:5][O:6]1)([CH2:14]3)[CH2:8]2)(=[O:28])=[O:27]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59374962[3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methanol

Product 1

HCID 59374979[3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo[3.3.1.03,7]non-1-yl]methyl methane sulfonateYield 89.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(2-Methyl-1,3-dioxolan-2-yl)tricyclo[3.3.1.03,7]non-1-yl]methanol (2.0 g, 8.47 mmol) obtained in step IV, in THF (35 mL) at ice bath temperature, was sequentially added triethylamine (3.5 mL, 25.4 mmol), DMAP (52 mg, 0.42 mmol), and methanesulfonyl chloride (0.97 mL, 12.7 mmol). After stirring the reaction mixture at the same temperature for 0.5 h, it was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain title compound [3-(2-Methyl-1,3-dioxolan-2-yl) tricyclo[3.3.1.03,7]non-1-yl]methyl methane sulfonate (2.4 g) in 90% yield as viscous liquid. m/z (M+1) 317. IR cm−1 2954, 1461, 1356, 1216, 1174, 1048, 756. 1H NMR (CDCl3) 300 MHz δ 4.15-3.90 (m, 4H), 3.00 (s 3H), 2.44-2.36 (m 2H), 1.89-1.79 (m, 2H), 1.78-1.42 (m, 8H), 1.29 (s, 3H). 13C NMR (CDCl3) 75 MHz δ 112.1, 76.3, 64.95, 64.9, 57.3, 46.6, 45.3, 44.9, 44.5, 42.9, 39.8, 36.9, 36.7, 36.3, 20.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f5f2d76fb0aa4b1c993427e2c71b8bb9
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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