1,2-Dichloroethane → 1-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanone

HRID 906909Notes

Reaction equation

HRID 906909 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]2[CH2:45][NH:44][CH2:43][CH:42]2[C:46](=[O:48])[CH3:47])[CH:37]=[CH:38][C:39]=1[Cl:40]>C(Cl)Cl>[Cl:33][C:34]1[CH:35]=[C:36]([CH:41]2[CH2:45][N:44]([C:7]([C:6]3[CH:5]=[N:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)=[O:9])[CH2:43][CH:42]2[C:46](=[O:48])[CH3:47])[CH:37]=[CH:38][C:39]=1[Cl:40]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5924996-Methoxynicotinic acidHCID 671317481-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-ethanone

Product 1

HCID 671314081-[(3SR,4RS)-4-(3,4-Dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanoneYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-methoxy-nicotinic acid (0.53 g, 3.40 mmol) in CH2Cl2 (15 mL) were added EDC (0.659 g, 3.40 mmol), HOBt (0.465 g, 3.40 mmol) and Et3N (0.59 mL, 4.3 mmol). After one hour at RT was added 1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanone (XIII-1) (0.74 g, 2.90 mmol) and stirring was continued over night. The reaction mixture was then poured onto water and extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 and concentrate under vacuo. Flash chromatography (SiO2, EtOAc/H, 1:1) afforded 0.64 g (57%) of the title product as a white solid. ES-MS m/e: 393.1 (M+H+).

Workup

  1. waitwas continued over night
  2. additionThe reaction mixture was then poured onto water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrate under vacuo

Sources & evidence

ORD record
ord-dee2862cd0824d6390c8e4dce09eb096
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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