Hydrochloric Acid → HCID 69177805, compound

HRID 1624304Notes

Reaction equation

HRID 1624304 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1([CH2:14][N:15]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]2=[O:25])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.Cl>C1COCC1.[NH4+].[Cl-]>[OH:8][CH2:9][CH2:10][C:11]1([CH2:14][N:15]2[C:16](=[O:25])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]2=[O:24])[CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69156589HCID 69156589, compound

Product 1

HCID 69177805HCID 69177805, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 2-{1-[2-(tert-butyldimethylsilyloxy)-ethyl]-cyclopropylmethyl}-isoindole-1,3-dione (0.24 g, 0.68 mmol) in THF (3 mL) was added 1.0 M HCl (3 mL). The resultant solution was stirred, at room temperature, for 3 hours. The mixture was diluted with saturated aqueous NH4Cl (10 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The crude material was purified by column chromatography on silica gel (2:1 hexanes-ethyl acetate) and provided 0.146 g (88%) of 2-[1-(2-hydroxy-ethyl)-cyclopropylmethyl]-isoindole-1,3-dione as a white solid. 1H NMR (CDCl3) δ 0.29-0.35 (m, 2H), 0.59-0.62 (m, 2H), 1.41 (t, 2H, J=6.6 Hz), 2.80 (br s, 1H), 3.53 (s, 2H), 3.76 (t, 2H, J=6.6 Hz), 7.59-7.63 (m, 2H), 7.69-7.74 (m, 2H);

Workup

  1. extractionextracted with CH2Cl2 (3×20 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography on silica gel (2:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-0298de6046394bd28b5c14ccb5271511
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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