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

HRID 1517683Notes

Reaction equation

HRID 1517683 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>C(Cl)Cl>[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

4

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (3.7 mL, 1.0 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) (0.49 g, 1.6 mmol) in CH2Cl2 (32 mL), and stirred overnight at room temperature. The excess BBr3 was quenched with the dropwise addition of H2O (10 mL), and washed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL). The organic extract was dried over MgSO4 and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C15H18ClNO3+H: 296, observed: 296.

Workup

  1. customThe excess BBr3 was quenched with the dropwise addition of H2O (10 mL)
  2. washwashed with saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd78fb54889e4ccf96de91f2a43f851c
Source dataset
uspto-grants-2012_07
Patent number
US08232311B2

Reaction notes

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