Water → HCID 57270949, compound

HRID 439852Notes

Reaction equation

C[O:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:16](=[CH:17][C:18]=1[CH3:19])[CH:8]1[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:7]1[CH2:6]2.B(Br)(Br)Br.O>ClCCl.C(O)C>[OH:2][C:3]1[C:4]([CH3:20])=[C:5]2[C:16](=[CH:17][C:18]=1[CH3:19])[C@H:8]1[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C@H:7]1[CH2:6]2

Participants

Conditions

Temperature: -78 °C

Procedure

Under anhydrous conditions, 4b,5,9b,10-tetrahydro-2-methoxy-1,3-dimethylindeno[1,2-b]indole (76 mg, 0.29 mmol) was dissolved in dry dichloromethane (DCM, 1 cm3) into which a small amount of ethanol had been added. The solution was cooled to -78° C., and a solution of boron tribromide in DCM (0.5 cm3 of 1M solution) added. The reaction was slowly warmed to room temperature, reaction occurring at 0° C. After 30 minutes at 10° C., water (1 cm3) was added cautiously, and the reaction stirred for 15 minutes. The mostly solid material was exhaustively extracted between DCM and a saturated solution of sodium bicarbonate. The DCM layer was dried (Na2SO4), and filtered through a pad of flash silica to yield a colourless solid. Yield: 73 mg, 100% .M.p. 178°-180° (dec). 1H NMR (CDCl3) δ: 7.16 (1H, d, J = 7.3 Hz), 6.99 (1H, ddm), 6.94 (1H, s), 6.73 (1H, ddm, J=7.3, 1.1 Hz), 6.60 (1H, d, J=7.7 Hz), 5.20 (1H, d, J=8.4 Hz), 4.4 (2H, br), 4.15 (1H, ddm), 3.38 (1H, dd, J=16.1, 8.3 Hz), 3.09 (1H, dd, J=16.2 Hz), 2.21 (3H, s), 2.12 (3H, s).

Workup

additionhad been added
temperatureThe reaction was slowly warmed to room temperature
customreaction
customoccurring at 0° C
extractionThe mostly solid material was exhaustively extracted between DCM
dry with materialThe DCM layer was dried (Na2SO4)
filtrationfiltered through a pad of flash silica
customto yield a colourless solid

Sources & evidence

ORD record: ord-f935ec6cec674187b6cb4956de50d252
Source dataset: uspto-grants-1996_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05516788

Reaction notes

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