Triethylamine → 2-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate

HRID 255161Notes

Reaction equation

HRID 255161 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH2:5]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.C(Cl)(Cl)Cl.CO>[CH3:25][S:26]([O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:17])[CH2:6][CH2:5]1)(=[O:28])=[O:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 62657Potassium Phosphate, TribasicHCID 45076484[1-(2-Hydroxy-ethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester2×

Product 1

HCID 568344782-(4-((Tert-butoxycarbonyl)amino)piperidin-1-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of tert-butyl [1-(2-hydroxyethyl)piperidin-4-yl]carbamate (Intermediate 7, 1.7 g, 7 mmol) in dry dichloromethane (20 mL) and triethyl amine (1.4 mL, 9.8 mmol) was treated at 0° C. with methanesulfonyl chloride (0.65 mL, 8.4 mmol). After 45 minutes the reaction was complete by TLC (chloroform/methanol 6:1, rf 0.54). Potassium phosphate buffer (pH 7, 1M, 50 mL) was added, dichloromethane was removed under reduced pressure and it was extracted with ice-cold ethyl acetate (2×100 mL) and dried over sodium 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. customdichloromethane was removed under reduced pressure and it
  2. extractionwas extracted with ice-cold ethyl acetate (2×100 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude preparation of the mesylate

Sources & evidence

ORD record
ord-f2f21fd2e8974596b22006ce1e7a1c3e
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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