Sodium Hydroxide → Dihydrocholesterol

HRID 1721305

Reaktionsgleichung

Reaktionsgleichung von HRID 1721305
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C1COCC1.CO>[CH3:26][CH:24]([CH2:23][CH2:22][CH2:21][C@H:20]([C@@H:19]1[C@:28]2([CH3:36])[C@H:16]([C@H:15]3[C@H:31]([CH2:30][CH2:29]2)[C@:32]2([CH3:35])[C@H:12]([CH2:11][C@@H:10]([OH:9])[CH2:34][CH2:33]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1)[CH3:27])[CH3:25]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 251110Cholestanol benzoate

Produkt 1

HCID 6665DihydrocholesterolAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of pyridazine 12 (113 mg, 0.22 mmol) in THF (1 mL) and MeOH (2 mL) was treated with 1M NaOH (0.29 mL, 0.29 mmol) and allowed to stand at ambient temperature for 16 h. The solvent was evaporated at reduced pressure and the residue was treated with CH2Cl2 (50 mL) and a 10% Na2CO3 solution (20 mL). The organic layer was separated, dried over MgSO4, filtered, and evaporated to dryness. The residue was purified by flash chromatography on 4 g of silica gel 60 using MeOH/CHCl3 (5:95) giving 65 mg (72%) of 13, which crystallized from CH2Cl2 /acetone, mp 203°-205° C. 1H NMR: δ3.71 (m, 1H), 3.13 (dd, 1H, J=5.6, 13.4 Hz), 3.10 (dd, 1H, J=6.8, 16.5 Hz), 2.95 (dd, 1H, J=10.6, 16.3 Hz), 2.61 (dd, 1H, J=12.8, 17.9 Hz), 2.27 (dd, 1H, J=6.1, 11.0 Hz), 2.23 (ddd, 1H, J=3.6, 3.6, 13.4 Hz), 1.06 (s, 3H), 0.99 (d, 3H, J=6.2 Hz), 0.89 (d, 6H, J=6.6 Hz), 0.80 (s, 3H). IR (Nujol): 3301, 1626, 1554, 1035 cm-1. EIMS (m/z): 410 (M+), 395 (M-Me). Anal. (C27H42N2O): C, H, N.

Aufarbeitung

  1. customThe solvent was evaporated at reduced pressure
  2. additionthe residue was treated with CH2Cl2 (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography on 4 g of silica gel 60 using MeOH/CHCl3 (5:95)

Quellen und Nachweise

ORD-Eintrag
ord-897d3c4b38d14067be4826b8f6627324
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05510340

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