Nitrogen → (3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate

HRID 1044783Notes

Reaction equation

HRID 1044783 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[C:11]([CH2:15][OH:16])[CH:12]=[CH:13][CH:14]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:27][S:24]([O:16][CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:4]2([CH3:3])[O:5][CH2:6][CH2:7][O:8]2)[CH:10]=1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66820167[3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl]-methanol

Product 1

HCID 86649478(3-(2-Methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-methanol (1.68 g, 8.65 mmol) in dry CH2Cl2 (20 mL) was treated at 0° C. with Et3N (1.60 mL, 11.38 mmol) followed by DMAP (109 mg, 0.88 mmol) and Ms-Cl (0.80 mL, 10.13 mmol). After stirring at 0° C. for 0.5 h, the reaction was quenched with water (10 mL). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. The crude residue was purified by FC (hept-EA 9:1 to 0:1) to give pure (3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl)methyl methanesulfonate as a white solid. Part of this material (300 mg, 1.10 mmol) was dissolved in dry DMF (5 mL) and treated with NaN3 (220 mg, 3.35 mmol) at 80° C. until completion of the reaction. The reaction mixture was then cooled down to rt and partitioned between EA and water. The layers were separated and the org. layer dried over MgSO4, filtered and concentrated under reduced pressure to give crude 3-(azidomethyl)-(2-methyl-[1,3]dioxolan-2-yl)benzene as a yellow oil. LC-MS-conditions 02: tR=0.99 min.

Workup

  1. customthe reaction was quenched with water (10 mL)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customThe crude residue was purified by FC (hept-EA 9:1 to 0:1)

Sources & evidence

ORD record
ord-23576cf6e5b04111bc30fa15a5273fe0
Source dataset
uspto-grants-2013_10
Patent number
US08563714B2

Reaction notes

Loading…