Acetic Acid → [1-(4-Fluoro-benzylamino)-cyclopentyl]-acetic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1([NH2:10])[CH2:9][CH2:8][CH2:7][CH2:6]1.[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1([NH:10][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[CH2:6][CH2:7][CH2:8][CH2:9]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A solution of (1-amino-cyclopentyl)-acetic acid methyl ester (318 mg, 2.02 mmol) in anhydrous methanol (10 mL) was treated with 4-fluoro-benzaldehyde (0.27 mL, 2.56 mmol) and stirred at 25° C. under a nitrogen environment. After 10 min, glacial acetic acid (0.384 mL, 6.71 mmol) and sodium triacetoxyborohydride (1.1 g, 5.05 mmol) were added sequentially, and the resulting mixture was stirred at 25° C. for 18 h. The reaction was diluted with a saturated aqueous sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give [1-(4-fluoro-benzylamino)-cyclopentyl]-acetic acid methyl ester (270 mg, 50%) as a colorless oil. LC-MS (ESI) calculated for C15H20FNO2: 265.3, found 266.2 [M+H+].
Workup
- stirringthe resulting mixture was stirred at 25° C. for 18 h
- extractionextracted with ethyl acetate (3×20 mL)
- washThe combined organic layers were washed with brine (20 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-604010e13b0243edb0c0afd90d686099
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834009B2
Reaction notes
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