Acetic Acid → HCID 59555492, compound
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[CH:5]([CH2:11][NH2:12])[CH:6]1[CH2:10]CCC1.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.[C:23](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(=O)(O)[O-].[Na+]>[CH2:2]([O:3][C:4]([C:5]1([CH2:11][NH:12][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=2)[CH2:6][CH2:10]1)=[O:13])[CH3:23]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of (1-aminomethyl)-cyclopentyl-acetic acid methyl ester hydrochloride (626 mg, 4.37 mmol) in anhydrous methanol (20 mL) was treated with 4-fluoro-benzaldehyde (0.46 mL, 4.37 mmol) and stirred at 25° C. under a nitrogen environment. After 10 min, glacial acetic acid (0.83 mL, 14.5 mmol) and sodium triacetoxyborohydride (2.3 g, 10.9 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 (30 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give 1-[(4-fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid ethyl ester (870 mg, 79%) as a colorless oil. LC-MS (ESI) calculated for C14H18FNO2: 251.1, found 252.1 [M+H+].
Workup
- stirringthe resulting mixture was stirred at 25° C. for 18 h
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined organic layers were washed with brine (25 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-dfd112304ff142d98ca7ebe559847c14
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834009B2
Reaction notes
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