Dimethylalumanylium chloride → {4-[8-(2-Chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-phenyl}-acetic acid ethyl ester

HRID 2194117Notes

Reaction equation

HRID 2194117 reaction equation
[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2([CH2:31][CH2:32]OC)[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[O:14])=[CH:8][CH:7]=1)[CH3:2].[Cl-].C[Al+]C>C1(C)C=CC=CC=1.CCCCCCC>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH2:32][CH2:31][C:15]3([CH2:20][CH2:19][N:18]([S:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])(=[O:22])=[O:23])[CH2:17][CH2:16]3)[C:13]2=[O:14])=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 2

HCID 16686359Dimethylalumanylium chlorideHCID 59578103(4-{[1-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carbonyl]-amino}-phenyl)-acetic acid ethyl ester

Product 1

HCID 59578003{4-[8-(2-Chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-phenyl}-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8900HeptaneSolvent

Procedure

(4-{[1-(2-Chloro-benzenesulfonyl)-4-(2-methoxy-ethyl)-piperidine-4-carbonyl]-amino}-phenyl)-acetic acid ethyl ester (2.47 g) in toluene (50 ml) was treated with dimethylaluminium chloride in heptane (1 molar, 5 ml) under an argon atmosphere at RT, and then refluxed for 3 hours. The reaction was then cooled to RT partitioned between AcOEt and 1N aqueous HCl/water. The layers were separated, the organic layer dried over sodium sulphate and the solvent was removed in vacuo to give the desired {4-[8-(2-chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-phenyl}-acetic acid ethyl ester as a light brown solid. MS (EI): 491.2 (M+).

Workup

  1. temperaturerefluxed for 3 hours
  2. custompartitioned between AcOEt and 1N aqueous HCl/water
  3. customThe layers were separated
  4. dry with materialthe organic layer dried over sodium sulphate
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-abcb8dc587814be0a395a4e793270dee
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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