Hydrochloric Acid → Methyl 1-((6-hydroxynaphthalen-2-yl)methyl)azetidine-3-carboxylate

HRID 713927

Reaktionsgleichung

Reaktionsgleichung von HRID 713927
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][N:20]1[CH2:23][CH:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1)[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][N:20]1[CH2:23][CH:22]([C:24]([O:26][CH3:27])=[O:25])[CH2:21]1)[CH:13]=[CH:12]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 66926610Methyl 1-((6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)methyl)azetidine-3-carboxylate

Produkt 1

HCID 66925934Methyl 1-((6-hydroxynaphthalen-2-yl)methyl)azetidine-3-carboxylateAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-((6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)methyl)azetidine-3-carboxylate (4.5 g, 11.7 mmol) in methanol (50 mL) at 0° C. was added con. HCl (5 mL) dropwise. The reaction mixture was stirred at r.t for 1 h. The mixture was neutralized by sat. NaHCO3 and evaporated off most of solvent, extracted with DCM and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (DCM:MeOH=40:1), extracted with DCM and washed with brine, dried over Na2SO4 and concentrated to obtain crude product. The crude product was purified by silica gel chromatography (DCM:MeOH=40;1) to give the title compound (1.5 g, 47%) as a gray solid. ESI-MS (M+1)+: 272.0. 1H NMR (400 MHz, CDCl3) δ: 8.14 (s, 1H), 7.59-7.52 (m, 2H), 7.39-7.28 (m, 2H), 7.09-7.04 (m, 2H), 3.92 (s, 2H), 3.86-3.82 (m, 2H), 3.70 (s, 3H), 3.63-3.59 (m, 2H), 3.252-3.46 (m, 1H).

Aufarbeitung

  1. customevaporated off most of solvent
  2. extractionextracted with DCM
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain crude product
  7. customThe crude product was purified by silica gel chromatography (DCM:MeOH=40:1)
  8. extractionextracted with DCM
  9. washwashed with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated
  12. customto obtain crude product
  13. customThe crude product was purified by silica gel chromatography (DCM:MeOH=40;1)

Quellen und Nachweise

ORD-Eintrag
ord-50d56694ebc34e1bb1616ed03a1f00eb
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09186367B2

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