6,6,9-Trimethyl-9-azabicyclo nonan

Trimethyl-9-azabicyclo[3.3.1 ] nonan-30i-ol Methyl 0i,ai-di(2-thienyl)glycollate... 

A mixture of 1.0 g of 6,6,9-trimethyl-9-azabicyclo[3.3.1 ] nonan-3/3-ol, methyl 0i,0i-di-(2-thienyD-glycollate and 30 mg of metallic sodium is heated at 80°C to 90°C for about 2 hours under reduced pressure. After cooling, ether is added to the reaction mixture. The mixture is extracted with 10% hydrochloric acid. The aqueous layer is alkalified with sodium carbonate and reextracted with ethyl acetate. The extract is washed with water, dried and concentrated to dryness. The residue thus obtained is treated with hydrogen chloride by conventional manner. 2.0 g of the 0i,0i-di-(2-thienyl)glycollate of 6,6,9-trimethyl-9-azabicyclo-(3.3.1 ] nonan-3/3-ol hydrochloride are obtained. Yield 83%. 

Trimethyl-9-azabicyclo[3.3.1]nonan-3a-ol Methyl a,a-di(2-thienyl)glycolate... 

Chiral auxiliary for asymmetric radical addition and allylation. Curran, Re-bek et al.1 have prepared the chiral auxiliary 2 from 1 by manipulation of the carboxylic acid groups to provide ( )-2, enr/o-7-(2-benzoxazolyl)-l,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one. The racemic auxiliary is then resolved via its menthyl carbamate to provide both (R)- or (S)-2. 

Bach, T, Bergmann, H., Grosch, B., Harms, K., and Herdtweck, E., Synthesis of enantiomerically pure l,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-ones as chiral host compounds for enantioselective photochemical reactions in solution. Synthesis, 1395, 2001. 

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