3-Methoxybenzoic Acid → Pyrrolidine, 1-(3-methoxybenzoyl)-

HRID 1497000Notes

Reaction equation

HRID 1497000 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:8])[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 114613-Methoxybenzoic AcidHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 786913Pyrrolidine, 1-(3-methoxybenzoyl)-Yield 126.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methoxybenzoic acid (13.5 g, 88.8 mmol), pyrrolidine (9 mL, 133 mmol), HATU (33 g, 88.8 mmol) and DIEA (30 mL, 172 mmol) in DMF (100 mL) was stirred at room temperature for 2 h. The solution was added water and extracted with ethyl acetate (200 mL×3). The organic layer was dried and concentrated. The residue was purified by silica gel chromatography (eluted with petroleum ether:ethyl acetate=2:1 to 1:1) to give (3-methoxyphenyl)(pyrrolidin-1-yl)methanone (23 g, 100%) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate (200 mL×3)
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (eluted with petroleum ether:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-12be2ae3d58f4afbbf8902a6e803dd0c
Source dataset
uspto-grants-2015_12
Patent number
US09199947B2

Reaction notes

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