Hydrochloric Acid → methyl (Z)-(2S,3S,4S)-7-[4-hydroxy-2-(3-pyridyl)-tetrahydrofuran-3-yl]-4-heptenoate

HRID 1492015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1492015
[Si]([O:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@@H:10]1[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])(C(C)(C)C)(C)C.Cl>CO>[OH:8][C@@H:9]1[CH2:13][O:12][C@H:11]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[C@H:10]1[CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86748311HCID 86748311, Verbindung

Produkt 1

HCID 86748312methyl (Z)-(2S,3S,4S)-7-[4-hydroxy-2-(3-pyridyl)-tetrahydrofuran-3-yl]-4-heptenoateAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 25.7 g (0.0612 mol) of methyl (Z)-(2S,3S,4S)-7-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-4-heptenoate in 257 ml of methanol is bubbled with HCl gas for about 2 min to give a strongly acidic solution. The mixture is allowed to stand at 0° C. overnight and evaporated. The residue is dissolved in 100 ml of water and extracted with ethyl acetate (2×). The ethyl acetate extracts are discarded. The aqueous layer is diluted with 150 ml of methylene chloride and neutralized by portionwise addition of potassium carbonate. The layers are separated and the aqueous layer is extracted with methylene chloride (3×). The combined extracts are washed with brine, dried (MgSO4) and evaporated to give 16.6 g of methyl (Z)-(2S,3S,4S)-7-[4-hydroxy-2-(3-pyridyl)-tetrahydrofuran-3-yl]-4-heptenoate as an oil with elemental analysis: C,65.87; H,7.78; N,4.58 (theory: C,66.86; H, 7.59; N,4.58) and optical rotation [α]D 25=+9.44 (methanol) and mass spectrum m/z 306 (M+1) (cald. MW=305.38).

Aufarbeitung

  1. customto give a strongly acidic solution
  2. customevaporated
  3. dissolutionThe residue is dissolved in 100 ml of water
  4. extractionextracted with ethyl acetate (2×)
  5. additionThe aqueous layer is diluted with 150 ml of methylene chloride
  6. additionneutralized by portionwise addition of potassium carbonate
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with methylene chloride (3×)
  9. washThe combined extracts are washed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6e115fa6489946c9bf2f295262ec1269
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371096

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