Phthalic Anhydride → HCID 11032835, compound

HRID 588120Notes

Reaction equation

HRID 588120 reaction equation
[NH2:1][C@@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[C:11]1(=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:20])[O:12]1>C(Cl)Cl>[OH:4][CH2:3][C@@H:2]([N:1]1[C:11](=[O:12])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:20])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 1347972-Amino-2-phenylethan-1-ol

Product 1

HCID 11032835HCID 11032835, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

(S)-2-amino-2-phenylethanol (2 g, 14.58 mmol) and isobenzofuran-1,3-dione (2.267 g, 15.31 mmol) were combined in a 20 mL microwave tube, sealed and heated to 150° C. for 6 hrs. The tube was cooled to ambient temperature, dilluted with DCM, loaded directly onto a 50 g SNAP column and purified 10-60% hexane/EtOAc to provide (S)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione. MS: [M+H]+ m/z 268.

Workup

  1. customsealed
  2. temperatureThe tube was cooled to ambient temperature
  3. custompurified 10-60% hexane/EtOAc

Sources & evidence

ORD record
ord-d637004903034c39afe4412ef5198d42
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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