Methanesulfonyl chloride → tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

HRID 586388Notes

Reaction equation

HRID 586388 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][O:15][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 22647269tert-Butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (9.41 g, 0.048 mol) in dichloromethane (200 mL) at room temperature was added iPr2NEt (14.1 g, 0.110 mol), followed by MsCl (5.5 g, 0.048 mol). The reaction mixture was allowed to stir for one hour before concentrating and purifying the resulting residue by silica gel chromatography (1:1 hexane:ethyl acetate). The desired compound was obtained as an oil (11.06 g, 86%).

Workup

  1. concentrationbefore concentrating
  2. custompurifying the resulting residue by silica gel chromatography (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-6a9574c2328d40628d6fdf7d1e42f121
Source dataset
uspto-grants-2005_08
Patent number
US06936614B2

Reaction notes

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