Methanesulfonyl chloride → 1,4-Dioxaspiro[4.5]decan-8-ylmethyl methanesulfonate

HRID 252029Notes

Reaction equation

HRID 252029 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][O:12][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 100808381,4-Dioxaspiro[4.5]decan-8-ylmethanol

Product 1

HCID 99923011,4-Dioxaspiro[4.5]decan-8-ylmethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1,4-dioxa-spiro[4.5]dec-8-yl)-methanol (1.0 g, 5.8 mmol, 1.0 eq.) and ethyldiisopropylamine (17 mL, 3.0 eq.) in methylene chloride (4 mL) at 0° C. was added dropwise MsCl (0.46 mL, 1.0 eq.) and the resulting mixture was warmed to room temperature and stirred for 2 h. The reaction was quenched by addition of sat. NaHCO3 and the separated aqueous phase was extracted with 3× methylene chloride and 4×EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated to give a crude methanesulfonic acid 1,4-dioxa-spiro[4.5]dec-8-ylmethyl ester.

Workup

  1. customThe reaction was quenched by addition of sat. NaHCO3
  2. extractionthe separated aqueous phase was extracted with 3× methylene chloride and 4×EtOAc
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-999cd3399e14434a9034c78469177d36
Source dataset
uspto-grants-2011_01
Patent number
US07868002B2

Reaction notes

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