Tributylphosphine → [3-[2-[1-(5-Bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid methyl ester

HRID 420600Notes

Reaction equation

HRID 420600 reaction equation
[Br:1][C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][C:10]([CH2:18][CH2:19][OH:20])([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[N:4][CH:3]=1.[Cl:21][C:22]1[CH:23]=[C:24]([CH2:29][C:30]([OH:32])=[O:31])[CH:25]=[C:26](O)[CH:27]=1.[CH2:33](P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O.O1CCCC1>[CH3:33][O:32][C:30](=[O:31])[CH2:29][C:24]1[CH:23]=[C:22]([Cl:21])[CH:27]=[C:26]([O:20][CH2:19][CH2:18][C:10]2([N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[CH2:11][CH2:12][N:7]([C:5]3[S:6][C:2]([Br:1])=[CH:3][N:4]=3)[CH2:8][CH2:9]2)[CH:25]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 596446192-(3-Chloro-5-hydroxyphenyl)acetic acidHCID 66657888HCID 66657888, compound

Product 1

HCID 66657791[3-[2-[1-(5-Bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethoxy]-5-chlorophenyl]acetic acid methyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[1-(5-bromothiazole-2-yl)-4-pyrrolidine-1-ylpiperidine-4-yl]ethanol (1.30 g), (3-chloro-5-hydroxy phenyl)acetic acid (796 mg), tri-n-butylphosphine (0.99 mL), 1,1′-(azodicarbonyl)dipiperidine (1.00 g) and tetrahydrofuran (20 mL) was stirred at room temperature for 4 hours. To the reaction solution was added water and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (1.45 g). Yield: 74%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-77a9a51aa2d14ae2adadada3fe34aa34
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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