Ethyl chloroformate → HCID 86602872, compound

HRID 546323Notes

Reaction equation

HRID 546323 reaction equation
Cl[C:2]([O:4]CC)=[O:3].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:13]([CH2:21][CH3:22])[CH:14]3[CH2:18][NH:17][CH2:16][CH:15]3[C:19]=2[CH:20]=1>C(Cl)Cl>[CH2:16]([NH:17][C:2](=[O:3])[O-:4])[CH3:15].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH:13]([CH2:21][CH3:22])[CH:14]3[CH2:18][NH:17][CH2:16][CH:15]3[C:19]=2[CH:20]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 58598878HCID 58598878, compound

Product 1

HCID 86602872HCID 86602872, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (0.16 mL, 1.65 mmol) was added to a solution of 5-methoxy-8-ethyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 48, Step B) (0.24 g, 1.1 mmol) in CH2Cl2 (6 mL) at 0° C. The resulting solution was stirred overnight at room temperature. The reaction mixture was quenched with aqueous HCl solution (20 mL, 1.0 M) and the product was extracted with EtOAc (3×10 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% EtOAc-hexanes gradient to afford 40 mg (13%) of the subtitle compound. MS calculated for C17H23NO3+H: 290, observed: 290.

Workup

  1. customThe reaction mixture was quenched with aqueous HCl solution (20 mL, 1.0 M)
  2. extractionthe product was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-2fd6cee945f34e589a178ce2273ac2b4
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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