Boron tribromide → N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 546306Notes

Reaction equation

HRID 546306 reaction equation
B(Br)(Br)Br.[CH2:5]([NH:7][C:8](=[O:10])[O-:9])[CH3:6].C[O:12][C:13]1[C:14]([Cl:26])=[CH:15][C:16]2[CH:17]([CH3:25])[CH:18]3[CH2:22][NH:21][CH2:20][CH:19]3[C:23]=2[CH:24]=1>>[CH2:5]([NH:7][C:8](=[O:9])[O-:10])[CH3:6].[OH:12][C:13]1[C:14]([Cl:26])=[CH:15][C:16]2[CH:17]([CH3:25])[CH:18]3[CH2:22][NH:21][CH2:20][CH:19]3[C:23]=2[CH:24]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 86602844N-Ethylcarbamate 5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Procedure

BBr3 (0.3 mL, 0.30 mmol, 1 M in CH2Cl2) was added to a solution of N-Ethylcarbamate-5-methoxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 3, Step A) (46 mg, 0.15 mmol) at 0° C., and stirred overnight at room temperature. The reaction solution was quenched with H2O 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 C15H18ClNO3+H: 296, observed: 296.

Workup

  1. customThe reaction solution was quenched with H2O
  2. filtrationfiltered through an Extrelut column
  3. washThe column was washed with CH2Cl2
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d7fc441f9919445a87a1aa933afb3e29
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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