Triethylamine → 1-Tert-butyl 3-methyl 4-{3-[(methylsulfonyl)oxy]propyl}piperidine-1,3-dicarboxylate

HRID 1644417Notes

Reaction equation

HRID 1644417 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]1[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].ClCCl.CO>ClCCl.C(OCC)(=O)C.O>[CH3:29][S:30]([O:1][CH2:2][CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]1[C:18]([O:20][CH3:21])=[O:19])(=[O:32])=[O:31]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21226129Dichloromethane methanolHCID 667751251-tert-Butyl 3-methyl 4-(3-hydroxypropyl)piperidine-1,3-dicarboxylate2×

Product 1

HCID 866525391-Tert-butyl 3-methyl 4-{3-[(methylsulfonyl)oxy]propyl}piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-tert-butyl 3-methyl 4-(3-hydroxypropyl)piperidine-1,3-dicarboxylate (Intermediate 133, 460 mg, 1.53 mmol) in dry dichloromethane (5 mL) and triethyl amine (0.3 mL, 2.14 mmol) was treated at 0° C. with a solution of methanesulfonyl chloride (0.14 mL, 1.83 mmol) in dichloromethane (5 mL). After 2 hours minutes the reaction was complete by TLC (dichloromethane:methanol 10:1). The reaction was diluted with ethyl acetate and water. The layers were separated. The organic layer was washed with 0.1N HCl, water, saturated sodium bicarbonate, dried over magnesium sulfate. The solvent was removed under reduced pressure and the crude preparation of the mesylate was used without delay for the next step.

Workup

  1. customThe layers were separated
  2. washThe organic layer was washed with 0.1N HCl, water, saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude preparation of the mesylate

Sources & evidence

ORD record
ord-fb3f1020cf6b4cf5857df2bfa8d9bb69
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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