Phthalimide → tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)morpholine-4-carboxylate

HRID 602130

反応式

HRID 602130 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][O:41][CH:40]([CH2:44]O)[CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32].N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][O:41][CH:40]([CH2:44][N:24]2[C:20](=[O:30])[C:21]3=[CH:29][CH:28]=[CH:27][CH:26]=[C:22]3[C:23]2=[O:25])[CH2:39]1)=[O:37])([CH3:34])([CH3:32])[CH3:33]

参加物

7

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylateHCID 66777355Diethylazodicarboxylate toluene

生成物 1

HCID 58992660tert-Butyl 2-((1,3-dioxoisoindolin-2-yl)methyl)morpholine-4-carboxylate収率 97%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Triphenylphosphine (506 mg, 1.87 mmol) and phthalimide (275 mg, 1.87 mmol) were added to 4-(tert-butoxycarbonyl)morpholin-2-yl methanol (340 mg, 1.56 mmol) in tetrahydrofuran (3 mL). The mixture was stirred at room temperature for 5 min, followed by addition of a 40% diethyl azodicarboxylate/toluene solution (1.06 mL, 2.34 mmol) and stirring at room temperature for 4 hours. Subsequently, ethyl acetate was added and the mixture washed sequentially with tap water and brine. The mixture was then dried over magnesium sulfate and the solvent was evaporated. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->3:1) gave 524 mg (97%) of the desired compound as a colorless powder.

後処理

  1. stirringstirring at room temperature for 4 hours
  2. washthe mixture washed sequentially
  3. dry with materialThe mixture was then dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->3:1)

出典と根拠

ORDレコード
ord-68037ced14ef487da4480e0c343604ce
出典データセット
uspto-grants-2011_03
特許番号
US07902367B2

関連ノート

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