Methanol → 5-Hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-one

HRID 1761013Notes

Reaction equation

HRID 1761013 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][O:15]C)[CH2:6]2.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][OH:15])[CH2:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 22594208HCID 22594208, compound

Product 1

HCID 225942285-Hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-oneYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methoxy-2-(2-methoxy-ethyl)-2,3-dihydro-isoindol-1-one (150 mg, 0.68 mmol) and boron tribromide (1 M in CH2Cl2, 1.4 mL, 1.36 mmol) in CH2Cl2 (8 mL) at −78° C. was stirred for 16 h at RT. The mixture was then cooled to −78° C. and MeOH (25 mL) was added. After 1 h at −78° C. the mixture was evaporated and the residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 90:10) to afford the title product (42 mg, 32%) as a light orange solid. MS m/e=193.3 (M+).

Workup

  1. temperatureThe mixture was then cooled to −78° C.
  2. customAfter 1 h at −78° C. the mixture was evaporated
  3. customthe residue purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 90:10)

Sources & evidence

ORD record
ord-5bcfb6f5d8b14553859f12bfe81dedb6
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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