Benzene → rac-methyl (1R,2S)-2-aminocycloheptane-1-carboxylate hydrochloride
Reaction equation
[ClH:1].[NH2:2][C@H:3]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[C:10]([OH:12])=[O:11].[CH:13]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO.ClCCl>[ClH:1].[CH3:13][O:11][C:10]([C@@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:3]1[NH2:2])=[O:12]Participants
6
Conditions
- Temperature
- 25 °C
Procedure
cis-2-Amino-cycloheptanecarboxylic acid hydrochloride (0.75 g, 3.89 mmol) was dissolved in methanol (5 mL). Benzene (7.5 mL) was added followed by the dropwise addition of a 2.0 M solution of (trimethylsilyl)diazomethane in dichloromethane (3.5 mL). The yellow solution continued to stir at 25° C. for 20 min. The solution was concentrated in vacuo to afford a yellow powder. The powder was suspended in methanol (20 mL) and concentrated in vacuo to afford the desired product, cis-2-amino-cycloheptanecarboxylic acid methyl ester hydrochloride (0.8 g, 3.86 mmol, 99%), as a white powder. 1H NMR (400 MHz, D2O) δ: 1.33-1.86 (8H, m), 2.60-2.62 (1H, m), 2.75-2.78 (1H, m), 3.27-3.30 (1H, m), 3.39-3.44 (1H, m), 3.62 (3H, s).
Workup
- concentrationThe solution was concentrated in vacuo
- customto afford a yellow powder
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f9e0f1fd7ccc44908dea0d9bbcee1c20
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
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