Methanol → Methyl tricyclo[3.3.1.13,7]decane-2-carboxylate
Reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]([OH:13])=[O:12])[CH2:8]2.CO.[CH3:16][Si](C=[N+]=[N-])(C)C>C(OCC)(=O)C>[CH:3]12[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]([CH2:8]3)[CH:2]1[C:11]([O:13][CH3:16])=[O:12])[CH2:4]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of adamantane-2-carboxylic acid 1 (0.486 g, 2.70 mmol) in ethyl acetate (10 mL)/methanol (5 mL) was dropwise added (trimethylsilyl)diazomethane (1.348 ml, 2.70 mmol) and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated and purified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes).
Workup
- concentrationThe reaction mixture was concentrated
- custompurified by flash chromotography (silica 40 g, 0%-30% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-c789df7a103c489a92c5e6de38ea8c13
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889675B2
Reaction notes
Loading…