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Hydrochloric Acid → (3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one

HRID 371446
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HRID 371446 반응식
C(=O)([O-])[O-].[K+].[K+].[Si:7]([O:14][CH2:15][C@H:16]1[C@H:23]([O:24]C(=O)C2C=CC=CC=2)[CH2:22][C@H:21]2[C@@H:17]1[CH2:18][C:19](=[O:33])[O:20]2)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].Cl>CO>[Si:7]([O:14][CH2:15][C@H:16]1[C@H:23]([OH:24])[CH2:22][C@H:21]2[C@@H:17]1[CH2:18][C:19](=[O:33])[O:20]2)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2724503(3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

생성물 1

HCID 10613232(3aR,4S,5R,6aS)-4-(tert-Butyldimethylsilyloxy)methyl-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-one수율 76.4%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

1.845 g of anhydrous potassium carbonate is introduced into a solution of 11.716 g of the silyl ether produced in Example 1 in 122 ml of absolute MeOH, and the mixture is agitated under argon for 3 hours. The reaction solution is then cooled in an ice bath and gently combined dropwise with 1.86 ml of concentrated hydrochloric acid. Excess methanol is extensively concentrated under vacuum at room temperature, the residue is combined with 300 ml of methylene chloride, and the solution is dried over magnesium sulfate, filtered off, and concentrated. The oily residue is made to crystallize by trituration with hexane, thus obtaining 6.562 g of the title compound, mp 60.7° C.

후처리

  1. temperatureThe reaction solution is then cooled in an ice bath
  2. concentrationExcess methanol is extensively concentrated under vacuum at room temperature
  3. dry with materialthe solution is dried over magnesium sulfate
  4. filtrationfiltered off
  5. concentrationconcentrated
  6. customto crystallize by trituration with hexane

출처 및 근거

ORD 기록
ord-7f63074b83494eb291fe191d514c5e0a
출처 데이터셋
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04532236

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