Sodium borohydride → 11-Allyl-6-hydroxymethyl-11-aza-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-8-ol

HRID 272605

Reaktionsgleichung

Reaktionsgleichung von HRID 272605
C[O:2][C:3]([C:5]1[C:16]2[C:15](=[O:17])[CH:14]3[CH2:18][CH:10]([CH2:11][N:12]([CH2:19][CH:20]=[CH2:21])[CH2:13]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1)=O.[BH4-].[Na+]>C(O)C>[CH2:19]([N:12]1[CH2:11][CH:10]2[CH2:18][CH:14]([CH:15]([OH:17])[C:16]3[C:9]2=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:3][OH:2])[CH2:13]1)[CH:20]=[CH2:21]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 5983784611-Allyl-8-oxo-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-6-carboxylic acid methyl ester

Produkt 1

HCID 6880607411-Allyl-6-hydroxymethyl-11-aza-tricyclo[7.3.1.02,7]trideca-2,4,6-trien-8-olAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

11-Allyl-8-oxo-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene-6-carboxylic acid methyl ester (109 mg, 0.40 mmol) was stirred in ethanol (10 mL) and treated with NaBH4 (15 mg, 0.40 mmol). After 18 h, the reaction mixture was concentrated and treated with 1N HCl (50 mL) with stirring. After 30 min., the aqueous layer was extracted with Et2O (3×50 mL), basified with saturated aqueous Na2CO3 solution and extracted with EtOAc (3×50 mL). The organic layer was washed with saturated aqueous NaHCO3 solution (2×50 mL) and saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated to give an oil (90 mg, 90%). (TLC 35% EtOAc/hexanes Rf 0.23); 1H NMR (400 MHz, CDCl3) δ 7.27 (dd, J=7.5, 1.5 Hz, 1H), 7.18 (t, J=7.5 Hz, 1H), 7.01 (dd, J=7.5, 1.5 Hz, 1H), 5.62 (m, 1H), 5.27 (t, J=4.0 Hz, 1H), 5.05 (m, 1H), 4.88 (d, J=12.1 Hz, 1H), 4.41 (d, J=12.1 Hz, 1H), 4.27 (OH), 3.72 (OH), 3.31 (ddd, J=12.4, 2.5, 1.7 Hz, 1H), 2.85 (m, 3H), 2.52 (m, 1H), 2.38 (m, 1H), 2.05 (dd, J=11.4, 1.7 Hz, 1H), 1.80 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 143.2, 140.3, 139.1, 134.9, 128.9, 127.7, 127.2, 118.5, 68.7, 64.0, 61.5, 59.9, 55.1, 36.3, 33.3, 32.1; IR (cm−1) 3376, 3071, 2920, 2788, 1642, 1468, 1051, 796; APCl MS m/z 260.2 (M+1)+.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. additiontreated with 1N HCl (50 mL)
  3. waitAfter 30 min.
  4. extractionthe aqueous layer was extracted with Et2O (3×50 mL)
  5. extractionextracted with EtOAc (3×50 mL)
  6. washThe organic layer was washed with saturated aqueous NaHCO3 solution (2×50 mL) and saturated aqueous NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-84dabeab89f8479b8c3954964d708f31
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456177B2

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