Benzene → cis-2-amino-cyclooctanecarboxylic acid methyl ester
Reaction equation
[NH2:1][C@H:2]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:10]([OH:12])=[O:11].[CH:13]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO.C(OCC)C>[CH3:13][O:11][C:10]([C@@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:2]1[NH2:1])=[O:12]Participants
6
Conditions
- Temperature
- 25 °C
Procedure
cis-2-Amino-cyclooctanecarboxylic acid (0.65 g, 3.8 mmol) was dissolved in methanol (5 mL). Benzene (7.5 mL) was added followed by dropwise addition of a 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether (3.5 mL). The yellow solution was stirred at 25° C. for 45 min. The solution was concentrated in vacuo. The residue was dissolved in methanol (20 mL) and concentrated in vacuo to afford the desired product, cis-2-amino-cyclooctanecarboxylic acid methyl ester (0.66 g, 3.56 mmol, 94%), as a colorless oil. LC-MS (ESI) calcd for C10H19NO2 185.14, found 186.2 [M+H+].
Workup
- concentrationThe solution was concentrated in vacuo
- dissolutionThe residue was dissolved in methanol (20 mL)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-cafa8032175648e6a678742922ae5c24
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
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