Cyclohexanone → 2-Cyclohexylamino-cyclohexanecarboxylic acid ethyl ester
Reaction equation
Cl.[CH2:2]([O:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@@H:8]1[NH2:13])=[O:6])[CH3:3].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[CH2:2]([O:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:6])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
cis-2-Amino-cyclohexanecarboxylic acid ethyl ester hydrochloride (0.5 g, 2.407 mmol) was dissolved in methanol (25 mL). Cyclohexanone (0.236 g, 2.407 mmol) was added followed by acetic acid (0.1 mL). The solution was stirred at 25° C. for 10 min. Sodium cyanoborohydride (0.378 g, 6.018 mmol) was added and the mixture was stirred at 25° C. for 16 h. The mixture was poured into 1/2 saturated aqueous sodium bicarbonate solution (300 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude product, 2-cyclohexylamino-cyclohexanecarboxylic acid ethyl ester (0.38 g, 1.5 mmol, 62.4%), as a clear oil. LC-MS (ESI) calcd for C15H27NO2 253.20, found 253.9 [M+H+].
Workup
- stirringthe mixture was stirred at 25° C. for 16 h
- extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8141e6160912452bb37b650d759f19b1
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
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