Ammonium Chloride → HCID 66615727, Verbindung

Temperatur

0 °C

At −10° C., a mixture of (3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-3,3a,4,5,6,7-hexahydroazulen-1(2H)-one (53 mg, 0.243 mmol) and CeCl3.7H2O (90 mg, 0.243 mmol) in MeOH (5 ml) was treated with sodium borohydride (9.2 mg, 0.243 mg) and the resulting mixture was stirred at 0° C. for 20 min., poured into aqueous saturated NH4Cl solution (5 ml) and ice and extracted twice with diethyl ether (3 ml). The combined organic phases were washed with aqueous saturated NaHCO3 solution (3 ml), with aqueous saturated NaCl solution (3 ml), dried with MgSO4, filtered, and the solvent evaporated. FC (5 g SiO2, hexane/MTBE 10:0.1 to 10:0.2 to 10:0.5) of the crude product (52 mg, GC: 93:7 (1R)/(1S)-epimer) gave (1R,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (34 mg, 64%) and (1 S,3S,3aS,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulen-1-ol (1 mg, 2%).

1. extractionextracted twice with diethyl ether (3 ml)
2. washThe combined organic phases were washed with aqueous saturated NaHCO3 solution (3 ml), with aqueous saturated NaCl solution (3 ml)
3. dry with materialdried with MgSO4
4. filtrationfiltered
5. customthe solvent evaporated

ORD-Eintrag

ord-a15e3a68dceb434d8b05cef64b3d6bf6

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08883468B2