Hydrochloric Acid → HCID 89907099, compound

HRID 2271310Notes

Reaction equation

HRID 2271310 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[C:11](=[CH:14]N(C)C)[CH:10]2[CH2:18][CH:19]=[CH:20][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[O:22]1CCOCC1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[C:11](=[CH:14][OH:22])[CH:10]2[CH2:18][CH:19]=[CH:20][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89907390HCID 89907390, compound

Product 1

HCID 89907099HCID 89907099, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl-3-(dimethylaminomethylene)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]pyrrole-1-carboxylate III-1 (120 mg, 0.43 mmol) in dioxane (9 mL) was stirred with hydrochloric acid (2 M, 0.86 mL, 1.72 mmol) for 15 h at room temperature. The solution was diluted with ethyl acetate, washed with water and brine, dried, concentrated giving the desired compound as a colorless oil (101 mg, 93%); 1H NMR (400 MHz, CDCl3) 9.92 (1H, d), 7.05 (1H, d), 6.91 (1H, m), 5.71 (1H, m), 5.07 (1H, d), 3.46 (1H, dt), 2.87 (1H, dd), 2.31 (1H, m), 1.55 (9H, s). LCMS (Method A): 0.79 min; ES−250 (M−H+).

Workup

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2ac0e660763741e087333902bff58fd7
Source dataset
uspto-grants-2015_09
Patent number
US09119398B2

Reaction notes

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