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Dimethyl Sulfate → (4s,7r)-3-Methoxy-7,8,8-trimethyl-2-phenyl-4,5,6,7-tetrahydro-2h-4,7-methano-indazole

HRID 1437907
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HRID 1437907 반응식
S(OC)(O[CH3:5])(=O)=O.[C:8]1([N:14]2[C:22](=[O:23])[C:21]3[C@@H:20]4[C:24]([CH3:26])([CH3:25])[C@@:17]([CH3:27])([CH2:18][CH2:19]4)[C:16]=3[NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[OH-].[Na+].O>[CH3:5][N:15]1[C:16]2[C@@:17]3([CH3:27])[C:24]([CH3:26])([CH3:25])[C@H:20]([CH2:19][CH2:18]3)[C:21]=2[C:22](=[O:23])[N:14]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1.[CH3:5][O:23][C:22]1[N:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:15]=[C:16]2[C:21]=1[C@@H:20]1[C:24]([CH3:26])([CH3:25])[C@@:17]2([CH3:27])[CH2:18][CH2:19]1
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참가 물질

6

반응물 2

HCID 6497Dimethyl SulfateHCID 57941335(4s,7r)-2-Phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one2회

생성물 2

HCID 57941522(4s,7r)-1,7,8,8-Tetramethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one수율 20%HCID 69022310(4s,7r)-3-Methoxy-7,8,8-trimethyl-2-phenyl-4,5,6,7-tetrahydro-2h-4,7-methano-indazole수율 23%

시약·촉매·용매 2

HCID 962Water용매
HCID 14798Sodium Hydroxide용매

실험 절차

Dimethyl sulfate (0.4 mL, 4.1 mmol) was added to (4S,7R)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 1.00 g, 3.7 mmol) in 1 M NaOH (10 mL). The mixture was stirred at room temperature overnight and then diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried (magnesium sulfate), filtered, evaporated, and purified using an Analogix Intelliflash 280 system (Analogix, Inc., Burlington, Wis.) with an RS-12 column, eluting with 0-16% ethyl acetate/hexanes to give (4S,7R)-1,7,8,8-tetramethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (213 mg, 20%) as a white solid, (4S,7R)-3-methoxy-7,8,8-trimethyl-2-phenyl-4,5,6,7-tetrahydro-2H-4,7-methano-indazole (243 mg, 23%) as a yellow solid and unreacted starting material (243 mg, 24%).

후처리

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified
  7. washeluting with 0-16% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-89ddf294e8f544fb9e677e8f7d58e370
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07622492B2

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