4-Fluorobenzaldehyde → HCID 69062137, compound
Reaction equation
Cl.[CH3:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH:9]=[CH:8][C@@H:7]1[NH2:12])=[O:5].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:2][O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH:9]=[CH:8][C@@H:7]1[NH:12][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=1)=[O:5]Participants
Conditions
- Temperature
- 25 °C
Procedure
The crude cis-2-amino-cyclohex-3-enecarboxylic acid methyl ester hydrochloride (2.8 mmol) was dissolved in methanol (5 mL). 4-Fluoro-benzaldehyde (37.3 mg, 0.3 mmol) was added, followed by 4 Å molecular sieves (0.5 g) and sodium acetate (0.46 g, 5.6 mmol). After stirring at 25° C. for 15 min, sodium cyanoborohydride (0.37 g, 5.9 mmol) was added and the mixture was stirred at 25° C. for 16 h. The mixture was poured into a mixture of saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (200 mL). After shaking, both layers were passed through a plug of Celite. The organic layer was washed with saturated aqueous sodium bicarbonate solution (100 mL), followed by saturated aqueous brine solution (100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the crude product, cis-2-(4-fluoro-benzylamino)-cyclohex-3-enecarboxylic acid methyl ester (250 mg, 0.95 mmol, 34%), as a clear oil. LC-MS (ESI) calcd for C15H18FNO2 263.13, found 264.04 [M+H+].
Workup
- stirringthe mixture was stirred at 25° C. for 16 h
- stirringAfter shaking
- washThe organic layer was washed with saturated aqueous sodium bicarbonate solution (100 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0a8881b70ed2462f8a6402fe9b05c12b
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
Loading…