1-(AMINOMETHYL)-CYCLOPROPANECARBOXYLIC ACID ETHYL ESTER

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

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

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

Procedure: In a 500-mL Parr shaker vessel, Raney nickel (750 mg) was added to MeOH (30 mL). Ethyl 1-cyanocyclopropanecarboxylate (Aldrich; 2.0 g, 14.38 mmol) was added and the resulting mixture was shaken vigorously under an H2 atmosphere (50 psi) for 24 h. The mixture was subsequently filtered through Celite, washing the Celite pad with MeOH (2×20 mL). The combined filtrates were concentrated in vacuo to provide ethyl 1-(aminomethyl)cyclopropanecarboxylate (1.5 g, 10.48 mmol, 73% yield): 1H NMR (400 MHz, CDCl3): δ 4.13 (q, 2H, J=7.2 Hz), 3.67 (s, 1H), 3.44 (s, 1H), 2.74 (br s, 2H), 1.27-1.21 (m, 5H), 0.80-0.74 (m, 2H). m/z (ESI, +ve) 144.4 (M+H)+. The mixture was subsequently filtered through Celite washing the Celite pad with MeOH (2×20 mL) The combined filtrates were concentrated in vacuo

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

Procedure: Reaction of 1-aminomethyl-cyclopropanecarboxylic acid ethyl ester with cyclopentanone, sodium acetate and sodium triacetoxyborohydride in DCM gave 1-cyclopentylaminomethyl-cyclopropanecarboxylic acid ethyl ester

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

Procedure: Reaction of 1-aminomethyl-cyclopropanecarboxylic acid ethyl ester with cyclopentanone, sodium acetate and sodium triacetoxyborohydride in DCM gave 1-cyclopentylaminomethyl-cyclopropanecarboxylic acid ethyl ester

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

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

Procedure: According to the procedure described in the synthesis method of Compound V-1 with the modification that the reaction solvent was changed to CH2Cl2 and DIPEA (1.6 ml, 9.3 mmol) was added, ethyl 1-(aminomethyl)cyclopropanecarboxylate (880 mg, 6.2 mmol) was reacted with benzyl isocyanate (1.15 ml, 8.0 mmol) to obtain the title compound (1.64 g, 106%). described in the synthesis method of Compound V-1 with the modification that the reaction solvent was added

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

Procedure: According to the procedure described in the synthesis method of Compound V-1 with the modification that the reaction solvent was changed to CH2Cl2 and DIPEA (1.6 ml, 9.3 mmol) was added, ethyl 1-(aminomethyl)cyclopropanecarboxylate (880 mg, 6.2 mmol) was reacted with benzyl isocyanate (1.15 ml, 8.0 mmol) to obtain the title compound (1.64 g, 106%). described in the synthesis method of Compound V-1 with the modification that the reaction solvent was added

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

Procedure: To a solution of ethyl 1-cyanocyclopropanecarboxylate (1 g, 7.18 mmol) in ethanol-water-conc. ammonia solution (7 ml-350 μl-1 ml) was added raney nickel (ca. 350 μl) and the mixture was sittred for 24 hr at 50° C. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to obtain the title compound (690 mg, 67%). The reaction mixture was filtered through Celite the filtrate was concentrated in vacuo

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

Procedure: To a solution of ethyl 1-cyanocyclopropanecarboxylate (1 g, 7.18 mmol) in ethanol-water-conc. ammonia solution (7 ml-350 μl-1 ml) was added raney nickel (ca. 350 μl) and the mixture was sittred for 24 hr at 50° C. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo to obtain the title compound (690 mg, 67%). The reaction mixture was filtered through Celite the filtrate was concentrated in vacuo

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

Procedure: Reaction of 1-aminomethyl-cyclopropanecarboxylic acid ethyl ester with cyclopentanone, sodium acetate and sodium triacetoxyborohydride in DCM gave 1-cyclopentylaminomethyl-cyclopropanecarboxylic acid ethyl ester

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

Procedure: Reaction of 1-aminomethyl-cyclopropanecarboxylic acid ethyl ester with cyclopentanone, sodium acetate and sodium triacetoxyborohydride in DCM gave 1-cyclopentylaminomethyl-cyclopropanecarboxylic acid ethyl ester