Triethylamine → Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylate

HRID 1518457Notes

Reaction equation

HRID 1518457 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 58303455Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylateYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of benzyl 4-hydroxy-1-piperidinecarboxylate (3.55 mL, 23.4 mmol, Aldrich) and Et3N (7.18 mL, 51.5 mmol, Aldrich) in CH2Cl2 (25 mL) at room temperature was added a solution of methanesulfonyl chloride (1.99 mL, 25.8 mmol, Acros) in CH2Cl2 (25 mL) dropwise. The reaction mixture was stirred at room temperature for 1 h and washed with 1N HCl aqueous solution, H2O and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to yield 7.43 g of the desired product as a yellow oil. MS (ESI) 314 (M+H).

Workup

  1. washwashed with 1N HCl aqueous solution, H2O and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-274433c472cf456ebca9ec8143882b98
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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