Acetic Anhydride → (R)-N-[1-(4-Nitrophenyl)pyrrolidin-3-yl]acetamide

HRID 1441366Notes

Reaction equation

HRID 1441366 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][CH2:20][C@@H:19]([NH2:22])[CH2:18]2)=[CH:13][CH:12]=1)([O-:10])=[O:9].C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:21][CH2:20][C@@H:19]([NH:22][C:3](=[O:5])[CH3:2])[CH2:18]2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 68688649(3r)-1-(4-Nitrophenyl)pyrrolidin-3-amine trifluoroacetate salt

Product 1

HCID 67147876(R)-N-[1-(4-Nitrophenyl)pyrrolidin-3-yl]acetamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(3R)-1-(4-Nitrophenyl)pyrrolidin-3-amine trifluoroacetate salt (Method 41; 0.96 g, 3 mmol) and sodium acetate (0.245 g, 3 mmol) in acetic acid (10 ml) were reacted with acetic anhydride (0.57 ml, 6 mmol) for 18 hours at room temperature. After filtration and washing with ether gave the title compound as a yellow solid (0.63 g, 84%). NMR: 1.79 (s, 3H), 1.85-1.98 (m, 1H), 2.09-2.23 (m, 1H), 3.19-3.30 (m, 1H), 3.39-3.52 (m, 2H), 3.55-3.67 (m, 1H), 4.30-4.43 (m, 1H), 6.60 (d, 2H), 8.04 (d, 2H), 8.15 (d, 1H); m/z 250.

Workup

  1. filtrationAfter filtration
  2. washwashing with ether

Sources & evidence

ORD record
ord-c220db5672b442eeaea9c3b227ea9a85
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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