2,2-Dimethylpropane-1-sulfonyl chloride → 1-(2,2-Dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2194015Notes

Reaction equation

HRID 2194015 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][C:17]([CH3:24])([CH3:23])[CH2:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[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][C:17]([CH3:24])([CH3:23])[CH3:16])(=[O:21])=[O:20])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 125746322,2-Dimethylpropane-1-sulfonyl chlorideHCID 567539694-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 667872401-(2,2-Dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.72 g) in methylene chloride (40 ml) was added at RT under an argon atmosphere DMAP (0.75 g) and then dropwise 2,2-dimethyl-propane-1-sulfonyl chloride (0.57 ml). The reaction mixture was stirred 12 h at RT then partitioned between AcOEt and aqueous 1M HCl, the layers were separated and the aqueous layer washed with 2M aqueous KHCO3 then dried over Na2SO4. The solvent was evaporated off, the residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 40%) to give the desired 1-(2,2-dimethyl-propane-1-sulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.34 g) as a light yellow viscous oil.

Workup

  1. customthen partitioned between AcOEt and aqueous 1M HCl
  2. customthe layers were separated
  3. washthe aqueous layer washed with 2M aqueous KHCO3
  4. dry with materialthen dried over Na2SO4
  5. customThe solvent was evaporated off
  6. customthe residue purified by flash chromatography (AcOEt/heptane, gradient from 0 to 40%)

Sources & evidence

ORD record
ord-3a7af084099446a8802f671448494d85
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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