Acetic Acid → 5-Methyl-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020323Notes

Reaction equation

HRID 1020323 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.C(O)(=O)C.C(NC(=O)[O-])C.[CH3:19][C:20]1[CH:21]=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1>ClCCCl.C(Cl)Cl.O>[CH3:19][C:20]1[C:21]([Cl:8])=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 86602856HCID 86602856, compound

Product 1

HCID 585988585-Methyl-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

NCS (27 mg, 0.2 mmol) and acetic acid (1 mL) were added to a solution of N-Ethylcarbamate-5-methyl-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (50 mg, 0.2 mmol) in DCE (1 mL). The reaction solution was stirred for 3 hours at 60° C. The reaction was diluted with CH2Cl2 (3 mL) and H2O (3 mL) and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-60% ethyl acetate-hexanes gradient to afford the subtitle compound. MS calculated for C16H20ClNO2+H: 294, observed: 294.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-fc5ed8e2d36c484ba721115f05787ddd
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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