Boron tribromide → 8-Hydroxy-2-propyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole hydrobromide

HRID 5347Notes

Reaction equation

Cl.C[O:3][CH:4]1[CH:15]2[CH:11]([CH2:12][N:13]([CH2:16][CH2:17][CH3:18])[CH2:14]2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2.B(Br)(Br)[Br:20]>C(Cl)Cl>[BrH:20].[OH:3][CH:4]1[CH:15]2[CH:11]([CH2:12][N:13]([CH2:16][CH2:17][CH3:18])[CH2:14]2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

Conditions

Temperature: -78 °C

Procedure

The product from Example 9 (0.490 g) was dissolved in 25 ml methylene chloride and cooled to -78° C. To the reaction was added 0.69 ml BBr3. The reaction was warmed to 0° C. for 4 h and then cooled to -78° C. The reaction was quenched by the addition of 5 ml methanol and the solvent was evaporated. The resulting solid was recrystallized from ethanol and ether to yield 0.470 g white solid, mp: 187°-9° C. NMR (d6DMSO) δ0.88 (t, 3H), 1.65 (m, 2H), 2.60-4.10 (m, 10H), 6.65 (d, 1H), 6.70 (d, 1H), 7.05 (t, 1H).

Workup

temperatureThe reaction was warmed to 0° C. for 4 h
temperaturecooled to -78° C
customThe reaction was quenched by the addition of 5 ml methanol
customthe solvent was evaporated
customThe resulting solid was recrystallized from ethanol and ether

Sources & evidence

ORD record: ord-fb02e62a59a44836a806f3943ed12dcc
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244888

Reaction notes

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