Acetic Acid → Tert-butyl 2-(3-acetamidophenyl)pyrrolidine-1-carboxylate

HRID 1438106Notes

Reaction equation

HRID 1438106 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[CH3:22][C:23](O)=[O:24]>CCO.[Pt]>[C:23]([NH:1][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]=[CH:8][CH:9]=1)(=[O:24])[CH3:22]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57942920HCID 57942920, compound

Product 1

HCID 68452325Tert-butyl 2-(3-acetamidophenyl)pyrrolidine-1-carboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

4A (870 mg, 3.0 mmol) was hydrogenated in EtOH (12 mL) and HOAc (0.7 mL) with Pt/C (5% wt, 250 mg) using a H2 balloon for 2 days. After filtration and evaporation of solvent, the crude product was stirred in acetic anhydride (8.0 mL) for 20 min. After removal of acetic anhydride under high vacuum, the intermediate tert-butyl 2-(3-acetamidophenyl)pyrrolidine-1-carboxylate (316 mg, 35% yield for 2 steps) was obtained by chromatography (EtOAc/hexanes=1/1). This intermediate (310 mg, 1.0 mmol) was stirred in EtOAc (1.0 mL) and 4.0 N HCl/dioxane (4.4 mL, 18 eq) at rt for 1.0 h. After removal of solvent, 4B was obtained as HCl salt. 1H NMR (400 MHz, Methanol-d4) δ ppm 2.14 (s, 3H) 2.24 (m, 3H) 2.48 (m, 1H) 3.45 (m, 2H) 4.61 (m, 1H) 7.22 (d, J=7.47 Hz, 1H) 7.40 (t, J=7.69 Hz, 1H) 7.49 (m, 1H) 7.84 (s, 1H).

Workup

  1. customfor 2 days
  2. filtrationAfter filtration and evaporation of solvent
  3. customAfter removal of acetic anhydride under high vacuum

Sources & evidence

ORD record
ord-f552dfa81dcb4d91b853c2ca2537b97c
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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