Methanol → HCID 20069026, compound

HRID 982131Notes

Reaction equation

HRID 982131 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][CH:5]=1.B(Br)(Br)Br.C[OH:28]>C(Cl)Cl>[CH:4]([OH:3])=[O:28].[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][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 20069038HCID 20069038, compound

Product 1

HCID 20069026HCID 20069026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 44.1 mg. (0.159 mmol) of 6-methoxy-4-phenyl-2,3,4,5-tetrahydro-1H-benzo[e]isoindole hydrochloride, from Step 6, in 2 mL of methylene chloride is cooled to -78° C. and 0.64 mL of a 1M solution of boron tribromide in methylene chloride is added. The reaction is warmed to ambient temperature for 1 h and recooled to -78° C. before 1 mL of methanol is added. After warming to ambient temperature for 1 h, the solvents are removed in vacuo. Additional methanol (5 mL) is added and removed in vacuo. The product is chromatographed on silica gel, eluting with 18:1:1 ethyl acetate:formic acid: water to give 6-hydroxy-4-phenyl-2,3,4,5-tetrahydro-1H-benzo[e]isoindole formic acid salt.

Workup

  1. additionA suspension of 44.1 mg
  2. additionis added
  3. temperatureAfter warming to ambient temperature for 1 h
  4. customthe solvents are removed in vacuo
  5. additionAdditional methanol (5 mL) is added
  6. customremoved in vacuo
  7. customThe product is chromatographed on silica gel
  8. washeluting with 18:1:1 ethyl acetate

Sources & evidence

ORD record
ord-c69a6a0deaa74062bfc4d68acc2e1f8d
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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