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Triethylamine → 6-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020310
Notes
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Reaction equation

HRID 1020310 reaction equation
C(NC(=O)[O-])C.O[C:8]1[C:9]([Cl:21])=[CH:10][C:11]2[CH:12]([CH3:20])[CH:13]3[CH2:17][NH:16][CH2:15][CH:14]3[C:18]=2[CH:19]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC>CO.CS(C)=O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:21][C:9]1[CH:8]=[CH:19][C:18]2[CH:14]3[CH2:15][NH:16][CH2:17][CH:13]3[CH:12]([CH3:20])[C:11]=2[CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 116370656-Chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrroleYield 35%

Reagents, catalysts & solvents 4

HCID 167845
palladium(II) acetate
Catalyst
HCID 679Dimethyl SulfoxideSolvent
HCID 887MethanolSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole, o-trifluoromethanesulfonate (60 mg, 0.14 mmol), palladium(II) acetate (6 mg, 0.028 mmol) and 1,3-bis(diphenylphosphino) propane (12 mg, 0.035 mmol) in MeOH (0.5 mL) and DMSO (0.5 mL) was added Et3N (0.2 mL, 1.4 mmol). The resulting mixture was stirred for 2 hours at 80° C. then cooled to room temperature. The reaction mixture was diluted with EtOAc (5 mL) and then washed with H2O (2 mL). The organic extract was dried over MgSO4 and concentrated to afford 15 mg (35% yield) of the subtitle compound, which was used without further purification. MS calculated for C15H18ClNO2+H: 280, observed: 280.

Workup

  1. temperaturethen cooled to room temperature
  2. washwashed with H2O (2 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-95ebd61e21da44a88cdb38237562cc6f
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716324B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes