Acetic Acid → HCID 58598873, compound

HRID 1020325Notes

Reaction equation

HRID 1020325 reaction equation
[Cl:1]N1C(=O)CCC1=O.C(O)(=O)C.C(NC(=O)[O-])C.[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[CH:25]([CH3:33])[CH:26]3[CH2:30][NH:29][CH2:28][CH:27]3[C:31]=2[CH:32]=1>ClCCCl.C(Cl)Cl>[Cl:1][C:32]1[C:31]2[CH:27]3[CH2:28][NH:29][CH2:30][CH:26]3[CH:25]([CH3:33])[C:24]=2[CH:23]=[CH:22][C:21]=1[O:20][CH3:19]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 86602843N-Ethylcarbamate 5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 58598873HCID 58598873, compoundYield 7.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

N-chlorosuccinimide (0.39 g, 2.9 mmol) and acetic acid (3 mL) were added to a solution of N-ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, Step A) (0.80 g, 2.9 mmol) in DCE (3 mL). The resulting solution was stirred for 3 hours at 60° C. The reaction mixture was cooled to room temperature, diluted with CH2Cl2 (50 mL), and washed with H2O (50 mL). The organic extract was dried over MgSO4 and concentrated. The crude product was purified by column chromatography (SiO2) using a 0-35% EtOAc-hexanes gradient to afford 50 mg (6%) of the subtitle compound (The major product is N-ethylcarbamate-5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole, 78%). MS calculated for C16H20ClNO3+H: 310, observed: 310.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with H2O (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-59ace1f1222a49acb790aab65ca1104b
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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