Methanesulfonyl chloride → HCID 86661362, compound

HRID 383796Notes

Reaction equation

HRID 383796 reaction equation
[CH:1]1([C@H:7]2[CH2:12][C@@H:11]([CH2:13][OH:14])[CH2:10][N:9]([C:15]([O-:17])=[O:16])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C1COCC1>[CH:1]1([C@H:7]2[CH2:12][C@@H:11]([CH2:13][O:14][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:10][N:9]([C:15]([O:17][C:1]([CH3:7])([CH3:6])[CH3:2])=[O:16])[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86661363HCID 86661363, compound

Product 1

HCID 86661362HCID 86661362, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of tert-utyl cis-3-cyclohexyl-5-(hydroxymethyl)piperidine-1-carboxylate (431.1 mg) in THF (10 ml) was added TEA (405.0 ml) and MsCl (135.2 ml) at 0° C. After stirring at 0° C. for 1 hour, the insoluble material was filtered off through celite and washed with THF. The filtrate was concentrated to give the crude tert-butyl cis-3-cyclohexyl-5-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate as a pale brown oil.

Workup

  1. filtrationthe insoluble material was filtered off through celite
  2. washwashed with THF
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-58c33996ca54486ab409517be86376d6
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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