Methanesulfonyl chloride → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

HRID 887518Notes

Reaction equation

HRID 887518 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[S:16](Cl)([CH3:19])(=[O:18])=[O:17]>C(Cl)Cl>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 1-Boc-4-hydroxymethyl-piperidine in anhydrous CH2Cl2 (50 ml) and TEA (4.5 ml) and cooled to 0° C. Mesyl chloride (840 μl) was added and the mixture was stirred for 15 min then at RT for 45 min. The mixture was washed with brine/1N HCl and then brine, dried over Na2SO4, concentrated in vacuo and dried under high vacuum to provide 1-Boc-4-methylsulfonyloxymethyl-piperidine as a yellow orange thick oil.

Workup

  1. waitat RT for 45 min
  2. washThe mixture was washed with brine/1N HCl
  3. dry with materialbrine, dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-1196df0e838f44ed841e3a98a5c07f84
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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