N-Hydroxyphthalimide → 2-((1H-imidazol-2-yl)methoxy)isoindoline-1,3-dione

HRID 1821828

反応式

HRID 1821828 の反応式
Cl.[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][OH:8].O[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7][O:8][N:10]1[C:14](=[O:15])[C:13]2[C:12](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]1=[O:20]

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27762781H-imidazol-2-ylmethanol Hydrochloride

生成物 1

HCID 689843332-((1H-imidazol-2-yl)methoxy)isoindoline-1,3-dione収率 6.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice-cold solution of (1H-imidazol-2-yl)methanol hydrochloride (2.0 g, 15 mmol), N-hydroxyphthalimide (2.4 g, 15 mmol) and triphenylphosphine (4.0 g, 15 mmol) in THF (65 mL) was added a solution of diethyl azodicarboxylate (2.6 mL, 16 mmol) in THF (10 mL) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 1 day, most of the THF was removed under reduced pressure. The residue was partitioned between CH2Cl2 (75 ml) and H2O (30 mL). The organic layer was separated and washed with saturated NaHCO3 (75 mL) and saturated NaCl (20 ml), dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography (silica gel, CH2Cl2 to 95:5 CH2Cl2/MeOH) gave 2-(1H-imidazol-2-ylmethoxy)-1,3-dihydro-2H-isoindole-1,3-dione (240 mg, 6.5%) which was used directly in the next reaction.

後処理

  1. customThe stirred reaction mixture
  2. custommost of the THF was removed under reduced pressure
  3. customThe residue was partitioned between CH2Cl2 (75 ml) and H2O (30 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated NaHCO3 (75 mL) and saturated NaCl (20 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by column chromatography (silica gel, CH2Cl2 to 95:5 CH2Cl2/MeOH)

出典と根拠

ORDレコード
ord-1f4a7513e2314a8ca524810f33ae7df1
出典データセット
uspto-grants-2009_10
特許番号
US07608627B2

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