Methanol → Methyl tricyclo[3.3.1.13,7]decane-2-carboxylate

HRID 336602

Reaction equation

HRID 336602 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]2

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 3038022-Adamantanecarboxylic acid

Product 1

HCID 12600018Methyl tricyclo[3.3.1.13,7]decane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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

  1. concentrationThe reaction mixture was concentrated
  2. 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

Linked notes

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