Methanesulfonyl chloride → (R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride

HRID 1511005Notes

Reaction equation

HRID 1511005 reaction equation
[OH:1][N:2]=[C:3]([Cl:14])[C@H:4]1[CH2:8][O:7][C:6]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:5]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(C(C)C)C(C)C)C>C1COCC1>[CH3:15][S:16]([O:1][N:2]=[C:3]([Cl:14])[C@H:4]1[CH2:8][O:7][C:6]2([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[O:5]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86644146(R)-N-hydroxy-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride

Product 1

HCID 86644147(R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chlorideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-N-hydroxy-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride (10.4 g, 47.3 mmol) cooled to 0° C. in THF (150 mL) was added methanesulfonyl chloride (5.97 g, 52.1 mmol) followed by N-ethyl-N-isopropylpropan-2-amine (6.75 g, 52.1 mmol) and the reaction stirred for 1 hr at ambient temperature. The reaction was concentrated in vacuo. The material was dissolved in dichloromethane and chromatographed using 8:1 Hexane/EtOAc to 4:1 Hexane/EtOAc (2 columns) to give the (R)-N-(methylsulfonyloxy)-1,4-dioxaspiro[4.5]decane-2-carbimidoyl chloride as a viscous oil that solidified on standing (12 g, 40 mmol, 85% yield).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe material was dissolved in dichloromethane
  3. customchromatographed

Sources & evidence

ORD record
ord-4c87ed7cf2fa44bbbf88da4eab0a7032
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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