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Diethyl Ether → Methyl 3-Benzyl-1,2,3,3a,4,5-hexahydro-4-(2,2-dimethyl-3-hydroxypropyl)-7H-pyrrolo (2,3-d) carbazole-6-carboxylate

HRID 330615
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HRID 330615 반응식
[CH2:1]([N:8]1[CH:12]2[CH:13]([CH2:28][C:29]([CH3:40])([CH3:39])[CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH2:14][C:15]([C:24]([O:26][CH3:27])=[O:25])=[C:16]3[NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:11]23[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].C(OCC)C>C1COCC1.O>[CH2:1]([N:8]1[CH:12]2[CH:13]([CH2:28][C:29]([CH3:40])([CH3:39])[CH2:30][OH:31])[CH2:14][C:15]([C:24]([O:26][CH3:27])=[O:25])=[C:16]3[NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:11]23[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 14750128methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-[2,2-dimethyl-3-(t-butyldimethylsilyloxy)propyl]-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

생성물 1

HCID 14750129Methyl 3-Benzyl-1,2,3,3a,4,5-hexahydro-4-(2,2-dimethyl-3-hydroxypropyl)-7H-pyrrolo (2,3-d) carbazole-6-carboxylate
수율 97.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 873 mg (1.56 mmol) of methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-[2,2-dimethyl-3-(t-butyldimethylsilyloxy)propyl]-7H-pyrrolo(2,3-d)carbazole-6-carboxylate in 30.5 mL of THF and 15 mL of water was added 5.24 g (20 eq) of p-toluenesulfonic acid. The reaction mixture was stirred for 90 min. At 20° C. and saturated aqueous K2CO3 solution was added until a pH=9-10 was obtained. Ethyl ether (100 mL) was added and the two layers were separated. The aqueous layer was extracted once with 100 mL of ethyl ether and twice with 100 mL of CH2Cl2. The combined organic layers were dried over MgSO4 and the solvents evaporated in vacuo (aspirator). The crude product was purified by column chromatography on silica gel (40 g). Elution with CH2Cl2 followed by ethyl ether gave 0.678 g (97.5%) of the title compound as a white foam. TLC: (Silica) Rf 0.50 (ethyl ether), detection with CAS (blue with developing yellow center), UV (long and short wave length).

후처리

  1. customwas obtained
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted once with 100 mL of ethyl ether and twice with 100 mL of CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvents evaporated in vacuo (aspirator)
  6. customThe crude product was purified by column chromatography on silica gel (40 g)
  7. washElution with CH2Cl2

출처 및 근거

ORD 기록
ord-63690f5137354cfb8a0d5408d826618d
출처 데이터셋
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04897477

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