Phthalimide → N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimide

HRID 602121노트

반응식

HRID 602121 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15]O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][N:40]2[C:39](=[O:41])[C:38]3=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]3[C:36]2=[O:46])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23521554Tert-butyl 3-(hydroxymethyl)azepane-1-carboxylate

생성물 1

HCID 58992706N-[[1-(tert-Butoxycarbonyl)perhydroazepin-3-yl]methyl]phthalimide수율 72%

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

1-(tert-Butoxycarbonyl)perhydroazepin-3-yl methanol (1.13 g, 4.93 mmol) was dissolved in tetrahydrofuran (10 mL). To this solution, triphenylphosphine (1.60 g, 5.92 mmol) and phthalimide (871 mg, 5.92 mmol) were added and the mixture was stirred at room temperature for 5 min. A 40% toluene solution of diethyl azodicarboxylate (3.23 mL, 7.40 mmol) was then added and the mixture was stirred at room temperature for 4 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The extract washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.27 g (72%) of the desired compound as a colorless powder.

후처리

  1. stirringthe mixture was stirred at room temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract washed with brine
  4. dry with materialwas dried over magnesium sulfate
  5. customfollowed by evaporation of the solvent
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

출처 및 근거

ORD 기록
ord-5a699c5b9dd144ba9de0c8e26f7334a9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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