Water → [5-((Morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methanol methanesulfonate

HRID 10175Notes

Reaction equation

HRID 10175 reaction equation
[N:1]1([CH2:7][CH:8]2[O:12][N:11]=[C:10]([CH2:13][OH:14])[CH2:9]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>ClCCl>[CH3:24][S:25]([O:14][CH2:13][C:10]1[CH2:9][CH:8]([CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[O:12][N:11]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21978759[5-(Morpholin-4-ylmethyl)-4,5-dihydro-isoxazol-3-yl]methanol

Product 1

HCID 21041076[5-((Morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methanol methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [5-(morpholin-4-ylmethyl)-4,5-dihydro-isoxazol-3-yl]methanol (0.38 g) in dichloromethane was added dropwise diisopropylethylamine (0.33 mL) and methanesulfonyl chloride (0.15 mL). The resulting solution was stirred at room temperature for 3 h and treated with water. The layers were separated and the organic layer was dried (Na2SO4) en concentrated in vacuo to afford [5-((morpholin-4-yl)methyl)-4,5-dihydro-isoxazol-3-yl]methanol methanesulfonate, 0.52 g (˜100%). Rf 0.63 (CH2Cl2/MeOH/NH4OH 92/7.5/0.5).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4) en
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ada8fcd0db23492da513b03733d44d67
Source dataset
uspto-grants-2006_08
Patent number
US07094779B2

Reaction notes

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