Carbon Dioxide → HCID 86762097, compound

HRID 1039637Notes

Reaction equation

HRID 1039637 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]3[CH2:23][CH2:22]3)=[CH:15][CH:14]=1)[CH2:5]2.[C:25](=O)=[O:26].C[Li].C([Li])CCC>O.C(O)(=O)C.CN(C=O)C.C1COCC1>[CH:21]1([CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([C:12]([NH:11][C@H:6]3[CH2:5][C:4]4[C:8](=[CH:9][CH:10]=[C:2]([CH:25]=[O:26])[CH:3]=4)[CH2:7]3)=[O:24])=[CH:14][CH:15]=2)[CH2:23][CH2:22]1

Participants

9

Reactant 4

HCID 280Carbon DioxideHCID 66680630HCID 66680630, compoundHCID 178418339ButyllithiumHCID 178418348HCID 178418348, compound

Product 1

HCID 86762097HCID 86762097, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-((R)-5-bromoindan-2-yl)-4-cyclopropylmethoxybenzamide (6.70 g) and THF (67 ml) was cooled to −78° C. (dry ice bath), and a solution of methyllithium (7.5 ml; 3 M) was added dropwise. One minute after the addition had ended, a solution of butyllithium (10 ml; 2.5 M in toluene) was added dropwise. One minute after the addition had ended, DMF (3.8 g) and, after a further 30 seconds, acetic acid (1.5 ml) were added. After warming to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated. This afforded the product with the molecular weight of 335.41 (C21H21NO3); MS (ESI): 336 (M+H+).

Workup

  1. additionOne minute after the addition
  2. additionOne minute after the addition
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phases were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThis afforded the product with the molecular weight of 335.41 (C21H21NO3)

Sources & evidence

ORD record
ord-7b3e93ae3f91442280c6086a4d1b962b
Source dataset
uspto-grants-2013_10
Patent number
US08552199B2

Reaction notes

Loading…