Methanol → 6,7-dihydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole formic acid salt

HRID 54150

Reaction equation

HRID 54150 reaction equation
Cl.C[O:3][C:4]1[C:16]2[CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]3[CH2:12][NH:11][CH2:10][C:9]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[O:23][CH3:24].B(Br)(Br)Br.C[OH:30]>C(Cl)Cl>[CH:24]([OH:23])=[O:30].[OH:3][C:4]1[C:16]2[CH2:15][CH:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:13]3[CH2:12][NH:11][CH2:10][C:9]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 199610916,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro 1H-benz[e]isoindole hydrochloride

Product 1

HCID 199612146,7-dihydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole formic acid saltYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 54.5 mg (0.159 mmol) of 6,7-dimethoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benz[e]isoindole hydrochloride, from Step 6, in 2 mL of methylene chloride was cooled to -78° C. and 0.64 mL of a 1M solution of boron tribromide in methylene chloride was added. The reaction was warmed to ambient temperature for 1 h and cooled to -78° C. before 1 mL of methanol was added. After warming to ambient temperature for 1 h, the solvents were removed in vacuo. Additional methanol (5 mL) was added and removed in vacuo. The product was chromatographed on silica gel eluted with ethyl acetate/formic acid/water (18:1:1) to give 29.8 mg (58% yield) of the title compound as an off-white powder, m.p. 144° C.; MS DCI: 279 (M+H)+ ; 1H NMR (d6 -DMSO) δ: 2.95-3.15 (m, 2H), 3.6-3.9 (m, 3H), 4.1-4.3 (m, 2H), 6.43 (d, 1H, J=7.5 Hz), 6.62 (d, 1H, J=7.5 Hz), 7.1-7.3 (m, 5H), 8.3 (s, 1H).

Workup

  1. additionwas added
  2. temperatureAfter warming to ambient temperature for 1 h
  3. customthe solvents were removed in vacuo
  4. additionAdditional methanol (5 mL) was added
  5. customremoved in vacuo
  6. customThe product was chromatographed on silica gel
  7. washeluted with ethyl acetate/formic acid/water (18:1:1)

Sources & evidence

ORD record
ord-051de95c92634eebbdf405eaebd937ab
Source dataset
uspto-grants-1997_04
Patent number
US05621133

Linked notes

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