Methanol → HCID 15035852, Verbindung

HRID 1091201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091201
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][S:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[OH:18]>O>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][S:12](=[O:18])[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 1460497-Benzyl-3-thia-7-azabicyclo[3.3.1]nonane

Produkt 1

HCID 15035852HCID 15035852, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 200-mL flask was equipped with a magnetic stirrer, an ice bath, and a condenser with nitrogen inlet. To a stirred, chilled (5° C.) solution of the amine (27, 1.4 g, 6 mmol) in methanol (60 mL) was added dropwise a solution of NaIO4 (1.35 g, 6.3 mmol) in water (15 mL) over 30 min. After stirring for one hour, the suspension was filtered and washed with methanol (50 mL); the washings and filtrate were combined and concentrated to a residue which was partitioned between H2CCl2 and water (40 mL each). Additional extracts (HCCl3, 3×40 mL) of the aqueous layer were combined with the initial extract, and the solution was dried (Na2SO4) and concentrated to afford an oil which solidified upon standing. Recrystallization (HCCl3 /pentane) of the solid gave 1.15 g (76.9%) of crystalline (49); mp 140°-141° C. IR (KBr) cm-1 3085, 3065, 3030, 2955, 2920, 2895, 2815, 1495, 1020, 740, 705; 1H NMR (DCCl3) δ1.59 [bd, 1 H, H(9), J=13.3 Hz], 1.86 [bd, 1 H, H(9), J=13.2 Hz], 2.20 [d, 2 H, H(2,4)ax, J=11.7 Hz], 2.37 bs, 2 H, H(1,5)], 2.62 [d, 2 H, H(6,8)ax, J=12.0 Hz], 2.78 [d, 2 H, H(2,4)eq, J=11.8 Hz], 3.51 [d, 2 H, H(6,8)eq, J=11.7 Hz], 3.55 [s, 2 H, ArCH2 ], 7.26-7.39 (m, 5 H, Ar--H); 13C NMR (DCCl3) ppm 31.86 [t, C(9)], 32.59 [d, C(1,5)], 57.42 [t, C(2,4)], 58.59 [C(6,8)], 62.88 (ArCH2), 127.20, 128.39, 129.12, 137.67; 15N NMR (DCCl3) ppm 49.37 [N(7)]. Anal. Calcd. for C14H19NOS: C, 67.43; H, 7.68. Found: C, 67.61; H, 7.73.

Aufarbeitung

  1. customA 200-mL flask was equipped with a magnetic stirrer, an ice bath, and a condenser with nitrogen inlet
  2. filtrationthe suspension was filtered
  3. washwashed with methanol (50 mL)
  4. concentrationconcentrated to a residue which
  5. customwas partitioned between H2CCl2 and water (40 mL each)
  6. extractioninitial extract
  7. dry with materialthe solution was dried (Na2SO4)
  8. concentrationconcentrated
  9. customto afford an oil which
  10. customRecrystallization (HCCl3 /pentane) of the solid

Quellen und Nachweise

ORD-Eintrag
ord-027be3dce545495bb605f9bcd781feeb
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05084572

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