Ethyl cis-2-amino-1-cyclopentane carboxylate hydrochloride → cis-2-[(5-Fluoro-pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester
Reaction equation
Cl.[NH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=O)=[N:18][CH:19]=1.C([BH3-])#N.[Na+]>C(O)C.C(O)(=O)C>[CH2:11]([O:10][C:8]([C@@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[NH:2][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([F:13])=[CH:19][N:18]=1)=[O:9])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
A solution of ethyl cis-2-amino-1-cyclopentane carboxylate hydrochloride (0.250 g, 1.29 mmol) in ethanol (10 mL) was treated with 5-fluoro-pyridine-2-carbaldehyde, glacial acetic acid (10 drops), sodium cyanoborohydride (0.162 g, 2.58 mmol) and stirred for 72 h at 50° C. The reaction was extracted with ethyl acetate (100 mL) and washed with saturated aqueous sodium bicarbonate solution (100 mL). The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo, and purified by flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 0-10% methanol in dichloromethane) to afford the desired product, cis-2-[(5-fluoro-pyridin-2-ylmethyl)-amino]-cyclopentanecarboxylic acid ethyl ester (0.179 g, 0.678 mmol, 52.5%), as a light yellow oil. LC-MS (ESI) calcd for C14H19FN2O2 266.14, found 267.2 [M+H+].
Workup
- extractionThe reaction was extracted with ethyl acetate (100 mL)
- washwashed with saturated aqueous sodium bicarbonate solution (100 mL)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- custompurified by flash column chromatography (Teledyne Isco RediSep Flash Column 10 g; 0-10% methanol in dichloromethane)
Sources & evidence
- ORD record
- ord-f94f87a9043a4661a3f06db450272fda
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582626B2
Reaction notes
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