Ethyl Bromide → HCID 86602859, compound

HRID 508518Notes

Reaction equation

HRID 508518 reaction equation
Br[CH2:2][CH3:3].C([O-])([O-])=O.[K+].[K+].[CH2:10]([NH:12][C:13](=[O:15])[O-:14])[CH3:11].[OH:16][C:17]1[C:18]([Cl:30])=[CH:19][C:20]2[CH:21]([CH3:29])[CH:22]3[CH2:26][NH:25][CH2:24][CH:23]3[C:27]=2[CH:28]=1>CC#N.O.C(Cl)Cl>[CH2:10]([NH:12][C:13](=[O:14])[O-:15])[CH3:11].[CH2:2]([O:16][C:17]1[C:18]([Cl:30])=[CH:19][C:20]2[CH:21]([CH3:29])[CH:22]3[CH2:26][NH:25][CH2:24][CH:23]3[C:27]=2[CH:28]=1)[CH3:3]

Participants

7

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 86602859HCID 86602859, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Bromoethane (17 mL, 0.23 mmol) and K2CO3 (105 mg, 0.75 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (44 mg, 0.15 mmol) in CH3CN (1.5 mL). The reaction was stirred overnight at 70° C., diluted with H2O and CH2Cl2, and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was obtained without further purification. MS calculated for C17H22ClNO3+H: 324, observed: 324.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-30f0853a774045339e25efe4f0926a76
Source dataset
uspto-grants-2015_08
Patent number
US09096520B2

Reaction notes

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