Triethylamine → tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate

HRID 54544Notes

Reaction equation

HRID 54544 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.C(N(CC)CC)C>C(Cl)Cl>[C:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14][CH2:13]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 15229596tert-Butyl 4-(2-((methanesulfonyl)oxy)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methanesulfonyl chloride (0.51 ml) in methylene chloride (5 ml) was added dropwise to a mixture of 4-(2-hydroxyethyl)-1-tert-butoxycarbonylpiperidine (1.43 g) and triethylamine (0.91 ml) at 5° C. After stirring at ambient temperature for 1 hour, the mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 1-tert-butoxycarbonyl-4-(2-mesyloxyethyl)piperidine (1.37 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5cfeb3dd818c45089f6ebdb5dc7bffac
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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