methyl 2-(1-aminocyclopentyl)acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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+]. the resulting mixture was stirred at 25° C. for 18 h extracted with ethyl acetate (3×20 mL) The combined organic layers were washed with brine (20 mL) dried over sodium sulfate filtered concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of (1-amino-cyclopentyl)-acetic acid hydrochloride (363 mg, 2.02 mmol) in a 1:1 mixture of anhydrous methanol/benzene (20 mL) cooled to 0° C. under a nitrogen environment was treated dropwise via syringe with a 2.0 M solution of trimethylsilyldiazomethane in toluene (2.0 mL, 4.0 mmol). The reaction mixture was allowed to warm to 25° C., stirred for 1 h, and concentrated in vacuo to give (1-amino-cyclopentyl)-acetic acid methyl ester (311 mg, 98%) as a colorless oil. LC-MS (ESI) calculated for C8H15FNO2: 157.2, found 158.2 [M+H+]. to warm to 25° C. concentrated in vacuo