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

HRID 602130

반응식

HRID 602130 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-68037ced14ef487da4480e0c343604ce
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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