ethyl 4-bromo-2-methylbutanoate

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

Procedure: A mixture of 40.0 g. (0.19 mole) of ethyl 4-bromo-2-methylbutyrate (Tetrahedron 21, 2966 (1965)), 66.0 g. (0.76 mole) of morpholine and 750 ml. of benzene was heated at 60°C. for 5 hours and stirred at room temperature for a total of 40 hours. A colorless solid was removed by filtration, and the mother liquor was evaporated to give a colorless, mobile residue. This material was combined with 250 ml. of ether and filtered to remove a small amount of additional solid. The solution was concentrated and the residue distilled to give the desired material as 38.0 g. (93%) of colorless liquid (b.p. 71°-73°C. at 0.10 mm). A mixture of 40.0 g A colorless solid was removed by filtration the mother liquor was evaporated to give a colorless, mobile residue of ether and filtered to remove a small amount of additional solid The solution was concentrated the residue distilled

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

Procedure: A mixture of 40.0 g. (0.19 mole) of ethyl 4-bromo-2-methylbutyrate (Tetrahedron 21, 2966 (1965)), 66.0 g. (0.76 mole) of morpholine and 750 ml. of benzene was heated at 60°C. for 5 hours and stirred at room temperature for a total of 40 hours. A colorless solid was removed by filtration, and the mother liquor was evaporated to give a colorless, mobile residue. This material was combined with 250 ml. of ether and filtered to remove a small amount of additional solid. The solution was concentrated and the residue distilled to give the desired material as 38.0 g. (93%) of colorless liquid (b.p. 71°-73°C. at 0.10 mm). A mixture of 40.0 g A colorless solid was removed by filtration the mother liquor was evaporated to give a colorless, mobile residue of ether and filtered to remove a small amount of additional solid The solution was concentrated the residue distilled

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.5 g. (0.05 mole) of ethyl γ-bromo-α-methylbutyrate was combined with 17.0 g. (0.20 mole) of piperidine and 100 ml. of benzene and stirred for 16 hours at room temperature and heated at 60° C. for 4 hours. The reaction mixture was cooled and the colorless solid which appeared was removed by filtration. The mother liquor was concentrated to give ethyl α-methyl-γ-piperidinobutyrate as a mobile yellow liquid which distilled (b.p. 78° C. at 0.25 mm.) as 6.7 g. (63%) of colorless liquid. The nuclear magnetic resonance and infrared spectra were consistent with the desired compound. The reaction mixture was cooled the colorless solid which appeared was removed by filtration The mother liquor was concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10.5 g. (0.05 mole) of ethyl γ-bromo-α-methylbutyrate was combined with 17.0 g. (0.20 mole) of piperidine and 100 ml. of benzene and stirred for 16 hours at room temperature and heated at 60° C. for 4 hours. The reaction mixture was cooled and the colorless solid which appeared was removed by filtration. The mother liquor was concentrated to give ethyl α-methyl-γ-piperidinobutyrate as a mobile yellow liquid which distilled (b.p. 78° C. at 0.25 mm.) as 6.7 g. (63%) of colorless liquid. The nuclear magnetic resonance and infrared spectra were consistent with the desired compound. The reaction mixture was cooled the colorless solid which appeared was removed by filtration The mother liquor was concentrated

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

Procedure: A mixture of 40.0 g. (0.19 mole) of ethyl 4-bromo-2-methylbutyrate (Tetrahedron 21, 2966 (1965)), 66.0 g. (0.76 mole) of morpholine and 750 ml. of benzene was heated at 60°C. for 5 hours and stirred at room temperature for a total of 40 hours. A colorless solid was removed by filtration, and the mother liquor was evaporated to give a colorless, mobile residue. This material was combined with 250 ml. of ether and filtered to remove a small amount of additional solid. The solution was concentrated and the residue distilled to give the desired material as 38.0 g. (93%) of colorless liquid (b.p. 71°-73°C. at 0.10 mm). A mixture of 40.0 g A colorless solid was removed by filtration the mother liquor was evaporated to give a colorless, mobile residue of ether and filtered to remove a small amount of additional solid The solution was concentrated the residue distilled

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

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