Dichloromethane → 5-Cyclopropylmethoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020328Notes

Reaction equation

HRID 1020328 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].C(NC(=O)[O-])C.[OH:18][C:19]1[CH:20]=[CH:21][C:22]2[CH:23]([CH3:31])[CH:24]3[CH2:28][NH:27][CH2:26][CH:25]3[C:29]=2[CH:30]=1.C(Cl)[Cl:33]>CC#N.O>[CH:5]1([CH2:4][O:18][C:19]2[C:20]([Cl:33])=[CH:21][C:22]3[CH:23]([CH3:31])[CH:24]4[CH2:28][NH:27][CH2:26][CH:25]4[C:29]=3[CH:30]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 86602864N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 585988525-Cyclopropylmethoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

(Bromomethyl)cyclopropane (13 mg, 0.09 mmol) and K2CO3 (24 mg, 0.17 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (23 mg, 0.09 mmol) in CH3CN, and stirred overnight at 80° C. The reaction mixture was diluted with H2O and CH2Cl2, and filtered through an Extrelut column. The column was washed with CH2Cl2, and the filtrate was concentrated. The subtitle compound was obtained without further purification. MS calculated for C19H25NO3+H: 316, observed: 316.

Workup

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

Sources & evidence

ORD record
ord-0d88521fa7054d0ebbedccdcbaa071fd
Source dataset
uspto-grants-2014_05
Patent number
US08716324B2

Reaction notes

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