1-Propanesulfonyl chloride, 2-methyl- → 4-(2-Methoxy-ethyl)-1-(2-methyl-propane-1-sulfonyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2194013Notes

Reaction equation

HRID 2194013 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:16][CH:17]([CH3:23])[CH2:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([CH2:12][CH2:13][O:14][CH3:15])[CH2:7][CH2:8][N:9]([S:19]([CH2:18][CH:17]([CH3:23])[CH3:16])(=[O:21])=[O:20])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1822361-Propanesulfonyl chloride, 2-methyl-HCID 567539694-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 667870884-(2-Methoxy-ethyl)-1-(2-methyl-propane-1-sulfonyl)-piperidine-4-carboxylic acid ethyl esterYield 40.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (1 g) was dissolved in pyridine (15 ml) under an argon atmosphere at RT and 2-methyl-propane-1-sulfonyl chloride (0.728 g) was added and the mixture was stirred for 60 h at RT. The pyridine was evaporated off, the residue dissolved in AcOEt, washed with 0.05M HCl and brine. The layers were separated, the organic layer dried over sodium sulphate and concentrated. The crude product was purified by flash chromatography (AcOEt/heptane, gradient from 0 to 25%,) to give the desired 4-(2-methoxy-ethyl)-1-(2-methyl-propane-1-sulfonyl)-piperidine-4-carboxylic acid ethyl ester (0.63 g) as a yellow oil. MS (ESI): 336.18 (MH+).

Workup

  1. customThe pyridine was evaporated off
  2. dissolutionthe residue dissolved in AcOEt
  3. washwashed with 0.05M HCl and brine
  4. customThe layers were separated
  5. dry with materialthe organic layer dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (AcOEt/heptane, gradient from 0 to 25%,)

Sources & evidence

ORD record
ord-bd2bee382acc4df9884c2baceb6d2050
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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