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

HRID 546314Notes

Reaction equation

HRID 546314 reaction equation
B(Br)(Br)Br.[CH2:5]([NH:7][C:8](=[O:10])[O-:9])[CH3:6].C[O:12][C:13]1[CH:14]=[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[CH:14]=[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 86602843N-Ethylcarbamate 5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Product 1

HCID 86602864N-Ethylcarbamate 5-hydroxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (1.1 mL, 1.0 M in dichloromethane) was added to a solution of N-ethylcarbamate-5-methoxy-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 2, step A) (0.31 g, 1.1 mmol) in CH2Cl2 (10 mL) at 0° C., and stirred overnight. The excess BBr3 was quenched with the dropwise addition of water (2 mL), and washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organic extract was dried over MgSO4 and concentrated. The subtitle compound was obtained without further purification. MS calculated for C15H19NO3+H: 262, observed: 262.

Workup

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

Sources & evidence

ORD record
ord-2a15cf5d02414237953b1f2551d5c246
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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