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Methanol → [2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-methanol

HRID 1295355
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HRID 1295355 반응식
C([O:3][C:4]([C:6]12C[CH:10]1[CH2:9][N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)C.C(OC(C1[C@H](C2C=CC=CC=2)N(S(C2C=CC(C)=CC=2)(=O)=O)CC=1)=O)C.CC(C[AlH]CC(C)C)C.CO>C(Cl)Cl>[C:22]1([CH:7]2[C:6]([CH2:4][OH:3])=[CH:10][CH2:9][N:8]2[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 589073302-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl esterHCID 69337074(S)-2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

생성물 1

HCID 58907347[2-Phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrol-3-yl]-methanol수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-25 °C

실험 절차

To racemic intermediate 1, one enantiomer being (S)-2-phenyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester (1.8 g, 5.0 mmol), was dissolved in methylene chloride (60 mL) in a three necked flask equipped with an addition funnel and an internal thermometer. The mixture was cooled to −25° C., DIBAL (1M/toluene, 12.5 mL, 12.5 mmol) was added dropwise and the reaction stirred for an additional 0.5 hours. Methanol was added to the cold solution until gas evolution ceased and the solvents were then removed at reduced pressure. The residue was partitioned between a saturated solution of Rochelle's salt and methylene chloride. The organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using a gradient of 20% to 60% ETOAc/Hexanes to yield the title compound as a sticky foam (1.6 g, 98% yield).

후처리

  1. customequipped with an addition funnel
  2. customthe solvents were then removed at reduced pressure
  3. customThe residue was partitioned between a saturated solution of Rochelle's salt and methylene chloride
  4. washThe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed on silica gel using a gradient of 20% to 60% ETOAc/Hexanes

출처 및 근거

ORD 기록
ord-f781173d1846437ebbdbf294fb1807d2
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07241798B2

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