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Phthalimide → 1-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

HRID 1295357
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HRID 1295357 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[C@@:10]([CH2:14]O)([CH2:11]2)[C@@H:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]1(=[O:51])[NH:45][C:44](=[O:46])[C:43]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:42]12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([CH2:14][N:45]3[C:41](=[O:51])[C:42]4[C:43](=[CH:47][CH:48]=[CH:49][CH:50]=4)[C:44]3=[O:46])([CH2:11]2)[CH:9]1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 69336539(1S,2S,5S)-1-hydroxymethyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester

생성물 1

HCID 693429221-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester수율 97%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To racemic Intermediate 19, one enantiomer being (1S,2S,5S)-1-hydroxymethyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (0.40 g, 1.4 mmol), was added anhydrous THF (5 mL), triphenylphosphine (0.43 g, 1.6 mmol), phthalimide (0.30 g, 2.1 mmol), and diethylazodicarboxylate (0.22 mL, 1.7 mmol). The reaction was allowed to stir at room temperature for 16 hours. The solvent was removed at reduced pressure and the residue partitioned between saturated sodium bicarbonate solution and methylene chloride, the organics were washed with brine, dried over sodium sulfate, filtered, and concentrated to an oil. The material was purified by chromatography on silica by elution with a gradient of 5 to 20% EtOAc/Hexanes to give the title compound as an white solid (0.56 g, 97% yield).

후처리

  1. customThe solvent was removed at reduced pressure
  2. customthe residue partitioned between saturated sodium bicarbonate solution and methylene chloride
  3. washthe organics were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe material was purified by chromatography on silica by elution with a gradient of 5 to 20% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-ec889b950005468eadf3e601f7fd2a82
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07241798B2

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