ethyl 2-amino-2-ethylhexanoate

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

Procedure: Lithium aluminium hydride (22.2 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature. 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour The resulting suspension was filtered the filtrate concentrated

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product from step (c) (1mole) in 1N aqu. HCl (1.2 moles) was stirred for 10 minutes at room temperature, then washed with toluene. The pH of the remaining aqueous phase was adjusted to 7 using 12.5% w/v sodium hydroxide, then cooled to 10° C., further basified to pH 12 and extracted with toluene. The extracts were combined, washed with brine, dried and evaporated in vacuo. The residue was distilled to give the desired product as an oil (70-80% yield). washed with toluene extracted with toluene washed with brine dried evaporated in vacuo The residue was distilled

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

Procedure: Lithium aluminium hydride (22.22 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature. 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour The resulting suspension was filtered the filtrate concentrated

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

Procedure: Lithium aluminium hydride (22.2 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature. 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour The resulting suspension was filtered the filtrate concentrated

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product from step (c) (1mole) in 1N aqu. HCl (1.2 moles) was stirred for 10 minutes at room temperature, then washed with toluene. The pH of the remaining aqueous phase was adjusted to 7 using 12.5% w/v sodium hydroxide, then cooled to 10° C., further basified to pH 12 and extracted with toluene. The extracts were combined, washed with brine, dried and evaporated in vacuo. The residue was distilled to give the desired product as an oil (70-80% yield). washed with toluene extracted with toluene washed with brine dried evaporated in vacuo The residue was distilled

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

Procedure: Lithium aluminium hydride (22.22 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature. 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour The resulting suspension was filtered the filtrate concentrated

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product from step (c) (1 mole) in 1N aqu. HCl (1.2 moles) was stirred for 10 minutes at room temperature, then washed with toluene. The pH of the remaining aqueous phase was adjusted to 7 using 12.5% w/v sodium hydroxide, then cooled to 10° C., further basified to pH 12 and extracted with toluene. The extracts were combined, washed with brine, dried and evaporated in vacuo. The residue was distilled to give the desired product as an oil (70-80% yield). washed with toluene extracted with toluene washed with brine dried evaporated in vacuo The residue was distilled

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

Procedure: Lithium aluminium hydride (22.22 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour was added dropwise The resulting suspension was filtered the filtrate concentrated

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

Procedure: Lithium aluminium hydride (22.2 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature. 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour The resulting suspension was filtered the filtrate concentrated

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of the product from step (c) (1mole) in 1N aqu. HCl (1.2 moles) was stirred for 10 minutes at room temperature, then washed with toluene. The pH of the remaining aqueous phase was adjusted to 7 using 12.5% w/v sodium hydroxide, then cooled to 10° C., further basified to pH 12 and extracted with toluene. The extracts were combined, washed with brine, dried and evaporated in vacuo. The residue was distilled to give the desired product as an oil (70-80% yield). washed with toluene extracted with toluene washed with brine dried evaporated in vacuo The residue was distilled

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

Procedure: Lithium aluminium hydride (22.22 g) was added to anhydrous diethyl ether (450 ml) under nitrogen. The product from (d) (129.0 g) was diluted with diethyl ether (40 ml) and added dropwise. The reaction was refluxed for 1 hour then cooled to room temperature. 1M sodium hydroxide (23 ml) was added dropwise followed by deionised water. The resulting suspension was filtered and the filtrate concentrated to give the desired product as a colourless oil (87.9 g). 1H NMR consistent with the proposed structure. added dropwise The reaction was refluxed for 1 hour The resulting suspension was filtered the filtrate concentrated